


Patience Run Thin

by lordmonday



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Dean Winchester, Deepthroating, Dubious Consent, Face-Fucking, First Time, Hand Jobs, Internalized Homophobia, M/M, Public Humiliation, Public Sex, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester, Top Chuck Shurley, Top Crowley (Supernatural), Top Jack, Top Lucifer (Supernatural)
Language: English
Status: In-Progress
Published: 2019-07-17
Updated: 2020-03-20
Packaged: 2020-05-20 18:38:16
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 19
Words: 86,505
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19382473
Author URL: https://archiveofourown.org/users/lordmonday/pseuds/lordmonday
Summary: Dean gets invited out for a drink by the king of hell. What could go wrong?This was supposed to be a one shot, and will now be all the wonderfully porny SPN ideas I have floating around in my head. Mostly bottom!Dean with literally almost everyone else...but Crowley first.





	1. Apocalyptic Advantages

**Summary for the Chapter:**

> The King of Hell could have sacrificed himself to contain Lucifer...but what if there was a twist on that? And then there's Michael to deal with...plot without porn this time, sorry!

**Notes for the Chapter:**

> Newly edited, this is what happens first! If you want porn, skip to chapter 3 and beyond, but this explains how everyone got to where they are!

Everything had changed with one tiny idea...almost as if it was put there by an outside source, like some benevolent author had arbitrarily decided the story needed just a  _ little _ shift. And that idea had saved the King of Hell from stupidly sacrificing his life needlessly. 

 

You see, they were in the Other world, the slightly grayer and more apocalyptic one. And they needed a life to complete Crowley's spell. Now, being the noble, upstanding gentleman he was, Crowley of course considered giving up his own life. After all, this was Lucifer, the only being thus far who had rivaled his mother for the tippy top spot on his most hated list. But then Crowley shook himself, another idea popping into his head, and a bewildered Sam just stared at him incredulously as Crowley began to text.  

 

"Relax, Moose. All part of the plan...just have to hope I still have that spelled phone on me..." Crowley said, whispering the last bit to himself, grinning a few seconds later when, in a world with no cell towers, his text went through. It only took a few minutes for another Crowley, this one a little worse for the wear from the trials of this world, to appear before him. "Ah, perfect timing. Sam, why don't you go help your better half? He's not sounding so good, and I believe our salvation has arrived. Now then, dear brother, we need a little help."

 

A little bullshitting, a little literal backstabbing, and the spell, which required someone to take their own life, was properly fooled. Not many situations where that could have worked, but in a world full of available doppelgangers, Crowley figured there was a good chance. He got the hell out of dodge after that, giving a happy little wave to Lucifer and the boys, passing Castiel on his way through the portal and feeling the energies of the emerging Nephilim the second he stepped back into his own world.

 

The power coming from inside the house was blinding, and burned his true form the closer he got. He was just starting to think it might be a good idea to get behind something, or leave entirely, when Lucifer's babymomma finally popped. The blast from the birth of one of the most powerful beings on the planet sent Crowley flying through space, almost like a banishing spell, nearly ripping the demon to pieces as he was hurled thousands of miles away. It hurt, dear Lucifer did it hurt, but something kept him together, something...suspiciously human. Crowley didn't have time to think about it, the pain and fear pushing him to use the final bit of his strength to zap himself to one of his hidden safe-houses, and fall unconscious for quite some time...

 

______________________________________________________________________________________________________________________________________

 

Months passed, with Crowley slowly recovering from injuries that would normally be much more quick to heal. He used that time to research what he could about Nephilim, and the damage they could cause, while still staying hidden from most of the world. Winchester's included, no matter how often they blew up his phone with voicemails and texts. When the messages started to go from hunting and controlling the son of Lucifer, to helping and protecting their surrogate son, Jack...well, Crowley was intrigued. But Crowley was still hurt, and even when Lucifer was finally killed, he couldn't quite bring himself to come join his friends in celebration. However, he did send them a quick thank you text, with lots of hearts. The first indication he was alive since the birth of little Jack, which resulted in a stream of "fuck you"s and "the hell have you been you smarmy bastard?" and maybe a few begrudging "glad you're not dead" type messages that definitely did not make Crowley at all happy. In later communication, he tried his best to downplay his injuries, lying in his bed with sub-par silken sheets and being ever so thankful humans had created smartphones. 

 

You see, through this time, Crowley had not been entirely idle. The few loyal followers Crowley possessed worked on his orders as he healed, slowly gathering bits and pieces of a kingdom he could rule once again. The Knights of Hell and Lucifer had destroyed much of what he had formerly had, but solely from the little piece of technology that fit in his hand, Crowley rebuilt. He waited until he had enough strength that any run of the mill demon wouldn't be able to end him with a sneeze, and found himself with a surprisingly receptive little kingdom on his hands. Apparently, when the ranks of hell get decimated and intimidated by several thuggish rulers, demons remember how good they've had it in the past. 

 

After some dedicated reorganizing, the beating down of several small insurrections, and a few bribes and bedfellows later, Crowley's New Hell was on its way to becoming the best Hell the world had never seen. Ever since Jack's birth, something had changed within the restored king, something Crowley was purposefully avoiding confirmation of. But however much he ignored it, Crowley was fairly certain some of his demonic essence had been purified into something resembling a human soul. It was different than what Sam had done to him during the Trials, this didn't feel like he was becoming the human he once was. More like...he was himself, but with more emotion, more of a conscience...not that he let it influence him too much, but he could feel it there all the same. 

 

During his rebuilding, Crowley got messages from his mother and the Winchesters, mostly regarding Jack. The poor Nephilim had lost his grace, and it was killing him from the inside. With his mother on the case, Crowley knew there was nothing he could add to help besides his own research, but let the Winchesters know he was looking for anything that could help. It wasn't his fault there was so little lore on angel-human hybrids. The child died, and then returned, using his own soul to power his life. Which Crowley knew wasn't sustainable, and put several of his smartest demons (of which there were a very limited number) on the case. When questioned about why he was helping the Winchester's, Crowley replied: "They're the Winchesters, and their tenacious pet angel. They've taken everything thrown at them, and now have one of the most powerful beings on the planet as their adopted son. Do you really want to be on their  _ bad _ side?"

 

Many more months passed in Hell, which of course was very different from the time on Earth, but by the time Crowley found some interesting hidden bits of lore that could be of help to the Winchesters, his kingdom was stable enough that he could leave it on its own. Unfortunately, Dean was having Michael problems, and Sam was texting him frantically about Dean and a head injury that Castiel couldn't heal. Even the angel texted him for help, so Crowley decided now was as good a time as any to finally return topside. And so, to the bunker he went. 

"...well. Isn't this touching?" Crowley said softly, Sam looking up from where he was cleaning Dean's wound, the older Winchester not moving from his spot in the bunker's hospital bed. "And here I am without a get well card and flowers. Hello, Moose. What has your brother gotten himself into this time?" he continued, Sam's response cut off by Dean surging up on the bed like he was having a seizure. Crowley quickly stepped over, his bravado gone and replaced with a surprising surge of...worry. A decidedly human emotion. The demon ignored it, placing his hand over Dean's forehead and shutting his eyes as he tried to feel out what was wrong, and not liking what he found.

"Anything? Cas couldn't see or heal past Michael, but Dean hit his head so-" Sam started, swallowing the end of his sentence. He and Dean had been through more scrapes than he could count, but this was different. There was more at stake, and Dean had never looked so vulnerable. Hurt on the outside, attacked from within. Crowley only took a moment before looking up at Sam, uncertainty in his eyes. 

"What spell did you, or my mother, use to contain Michael? I don't feel anything, and it won't be long before Dean's meager defenses give out." Crowley said, but a quick search of Sam's face said it all, and Crowley felt his faith in the boys shrivel to the size of a raisin. "No...don't tell me... _ please _ do not tell me the fate of humanity, of all  _ creation _ , has been dependent on the willpower of one questionably sane  _ Winchester _ . We're dealing with a bloody archangel! Have you two lost your minds?!" 

"Sam? Who is this?" a young, male voice said from behind him. Crowley turned, looking the boy up and down. Maybe eighteen, certainly not old enough to drink. Handsome, with a sweet innocence radiating off him like a beacon Crowley could spot a mile away. But there was something deeper, something hidden, that the demon couldn't quite put a finger on.

"Ah, the son of Lucifer. Finally we meet. Jack, was it?" Crowley said, looking him up and down again, searching for anything of the boy's father in him. Maybe something in the way he stood, or the line of his jaw, but certainly not the cockiness or lecherousness of his sire. He looked like someone the old Crowley wouldn't have hesitated to swindle a soul out of. "Crowley, king of hell. Afraid we'll have to save a proper introduction for later, the end of the world is once again approaching. And,  _ surprise _ , it's on account of the Winchesters. Will wonders never cease? Moose, make yourself useful and fetch my mother, as well as that archangel blade you've got lying around. Rumor has it it can kill an archangel without killing the host. And I’ve heard you have quite the collection of hunters around...might be best to send them away till we’ve got this taken care of. Not much they can do here, I’m afraid."

Sam nodded. getting up and leaving the room, looking a bit dazed, but with a bit more sense of purpose. Rowena and Cas had both acted like the situation was hopeless. At least Crowley was having him do something. Meanwhile, Jack frowned as Crowley lifted up Dean's shirt all the way up to his chest, and started feeling around.

"What are you doing?" Jack asked, coming closer but unsure if he could trust this new visitor. Sam certainly seemed to, and they had been talking about asking him for help, but why had he been away for so long if he was a trusted ally? Where had his help been when they needed it with Lucifer?

"Despite all of them being built roughly the same way, every human's organs are placed a bit differently. And given how many times this human has been put back together, it's better to be safe than sorry." Crowley said, knowing how most would see his hands feeling along the flat stomach and toned muscles of the hunter. Though, supposedly the child was rather innocent when it came to these things. Maybe he had no such assumptions. "If we're going to take out the world's strongest archangel, I'd rather Dean remain mostly intact. Unless you've got any of that archangel juice leftover for emergencies?"

"No." Jack said forlornly, looking down with guilt. "Any use of my powers now...burns up part of my soul. Cas and the others said it was irreversible and bad, but maybe in a situation like this..." the Nephilim muttered, almost to himself, walking up to Dean and raising a hand. Crowley gently grabbed it, stopping the young man's forward motion and slipping down Dean's shirt in the same motion.

"If I know anything about the Winchesters and their angelic guard dog, they would never forgive me for letting you burn up your own soul. If my idea doesn't work...well, then we'll talk. Hell, even I have a bit of a soul. Or something close, anyway. Not something you want to burn to a crisp at the first sign of danger. And besides, I've been doing my own research on your kind...I believe I'm rather close to a breakthrough to help you return to your formerly flighted form. Don't want to go messing up my little surprise now, do we?" Crowley said, keeping his voice low and convincing. Pouring on the charm. It seemed to work well enough, the kid looking at him with uncertainty for just a moment before nodding and walking a few steps away, putting both hands on the back of his neck and taking some deep breaths. Thankfully, Crowley didn't have to do any more convincing, as Rowena, Sam, and Castiel walked in, the angel holding the archangel blade tightly in one hand.

"Fergus...I wasn't sure I believed Samuel, but...well, here you stand. I feared...we didn't see you for so long, I wondered..." Rowena said, breaking out into a shockingly teary smile that spoke to that new, human-like part of Crowley. He stamped it down, nodding to her and swallowing subtly, keeping his face almost bored. 

"Yes, well...when one realizes the fate of the world has been left in the hands of these three bumbling buffoons, one gets off bed rest and goes to work." Crowley said, indicating the two scowling men who thankfully didn't notice his slightly nervous speech. His newly changed state of being seemed to leave him more vulnerable than usual to emotions, but he cleared his throat and got a hold of himself, holding out his hand for the golden blade in Castiel's hand. "Now, shall we save the apex of daddy issues and alcoholism from being used for the world's destruction?"

"What exactly will we be doing to Dean? The blade can only be wielded by an archangel, and all the rest have been exterminated. By us and each other." Castiel said, looking at the demon's hand with reluctance. He didn't...distrust Crowley, exactly. The demon had proved himself both traitor and ally in the past, but for the more recent chunk of time had been willing to risk his life for the group. But this was different, this was putting Dean's life in the hands of a demon, and even Castiel's long abandoned following of Heaven's law was poking from deep inside him and saying this was a bad idea. 

"Are they? I believe, Feathers, you're missing the obvious. Not that that's anything new for you. We have an archangel right in front of us, helpfully unconscious." Crowley said, indicating the still Winchester on the bed. Sam’s eyes lit up, and he let out a breath.

"Dean can wield the blade on himself, because he's got an archangel inside him." Sam said, almost bitterly, because he couldn't see another way. He turned to the witch at his side, swallowing and not meeting her eyes. "Would it work? Kill Michael and...let Dean survive? Like it did with Nick and Lucifer?"

"It's hard to say...that certainly wouldn't have been the way the blade would have been  _ intended _ to use. But the definitions of these things are rather literal, especially when it comes to Heaven. If it needs to be wielded by an archangel to work, then being in Dean's hand should allow it to possess the power to kill an archangel. If not...well, Michael should be able to heal Dean up, right as rain, before he...wipes out the planet." Rowena said, not looking too happy about it either, but she'd already tried looking at spell after spell to make this right. A weakened archangel she could harm, even banish given the right ingredients, but killing a fully powered one was out of even her vast reach for the time being. 

"And time is rather of the essence, considering the only thing keeping our assured destruction down is an unconscious, brain damaged Squirrel. Now, if you please, I've mapped out a spot that should give us the greatest hit to Michael's grace while avoiding anything of serious import to Dean." Crowley said, holding out his hand. Castiel hesitated, but then Dean surged up in bed, all his muscles tensing as a small, pained noise came from his throat. The angel shoved the blade in Crowley's hand before going to his friend's side, putting a hand against his forehead and attempting to keep him from hurting himself. Rather a backwards thought, Crowley mused, given what they were about to attempt. 

The demon stepped up on Dean's other side, pulling up his shirt and double checking the area briefly before positioning the blade just above the skin, looking at Castiel for confirmation. The angel did have a claim on the human, he supposed. Castiel nodded, grabbing Dean's right hand and holding it a few seconds longer than strictly necessary before wrapping the unconscious man's fingers around the hilt of the blade. Both beings looked at Sam, knowing the younger Winchester had the final say. The only true human in the room walked to the foot of the bed, his face heavy, and nodded. Crowley positioned his hand atop the blade as Castiel kept the possessed man's fingers wrapped tight around it, hesitating for just a few seconds before starting to lower the blade. If they failed this, Dean would perish by their own hands...

And with such an invitation, how could an archangel refuse? Their attempt to sink the blade lower was stopped by Dean's hand freezing in place, their friend's eyes opening and gazing around at all of them for a moment in fear, before flashing with blue light. A smile that was wrong for the face it was on came over Michael’s face. He thrust his chin forward, launching the Nephilum, witch, and hunter across the room. 

“Come on now, fellas. Is that how you’re supposed to treat your bestie? I’m wounded, or almost. Appreciate you two returning what’s mine.” Michael said flashing a distorted version of Dean’s charming grin at the two holding a blade over him, moving the weapon in the direction of Castiel’s heart in spite of the two supernatural beings trying to stop him. Engaged as they were, none of the three noticed Jack till he stood at the foot of the bed, blood dripping down his temple and off his jaw. 

“I didn’t know him for very long, but Gabriel was a  _ much  _ better uncle than you. And you killed him...I’m not going to let you do that to any more of my family.” Jack said, his eyes glowing with the white-hot power of his soul, his voice deathly calm as he lifted his hand and pointed at the blade. The grin disappeared from Michael’s face as the only weapon that could wound him turned back towards his bared stomach, and the most powerful being on the planet screamed as the blade plunged into him. 

Sam just managed to catch Jack as he collapsed, the Nephilum spent and unconscious. Michael’s light flared from inside him, flashing out of Dean’s eyes and mouth as he tried in vain to survive, the hospital bed acquiring two huge scorch marks in the shape of wings as the archangel perished. Crowley and Castiel panted from their spots a few feet from the bed, Crowley staring at the archangel blade now in his hand. Castiel regained his senses first and stepped forward, checking Dean’s pulse, his eyes glued to the Winchester’s face. A small cry of relief finally escaped him. 

“He’s alive...he’s alive.” he said loudly, then to himself. He looked over at Sam and Jack, swallowing and forcing himself to focus. “Jack, is he alright? He used his soul to...I don’t know what. Overpower Michael, somehow.” he continued, checking Dean’s injury. Jack’s direction had been perfect, the blade had hit the spot Crowley had recommended. Dean would be out of commission for a while, but his life shouldn’t be in danger.

“I think so...I don’t know how much of his soul he would need to do what he did, so we’ll find out when he wakes up, I guess.” Sam said, looking down at the young boy worriedly. Rowena walked over, muttering a spell to fix her bruised ribs before kneeling next to the two of them and getting some of Jack’s hair out of his face.

“The boy is strong, it’ll take more than killing an archangel to burn up his soul, mark my words.” Rowena said, before looking up at Fergus with a sparkle in her eyes as she rose. “Well, your majesty, seems we have you to thank for this wee victory. If anyone could pull this out of a hat, well...” she finished. Crowley smirked, looking over at Dean and letting his eyes linger on the man’s face, sensing the powerful heartbeat that refused to quit. Castiel looked up at him, locking eyes with the demon for a moment before nodding his thanks. A simple gesture, but one that meant a lot between the two. 

“Well, I best be getting off to hell...I have something cooking in the works that you all should be quite happy about. I’ll keep you posted, if you’ll do the same for me with tall, blonde, and dopey over here. Oh, and I’m keeping this. Consider it my fee.” Crowley said, wiggling the archangel blade to an incredulous group of onlookers and disappearing before anyone could protest. 


	2. Saving a Nephilum

**Summary for the Chapter:**

> Crowley's full of good ideas, some involving saving their latest little addition.

**Notes for the Chapter:**

> I'm gonna try to do some reorganizing, and likely a little editing of the first thing I posted, to make it fit better. Sorry for the changes and whatever inconsistencies there are, I wasn't expecting to turn it into a big story! Bit be prepared for porn in the future. ;P

Dean’s face was covered in sweat before him, bathed in moonlight, his lips parted slightly. His pupils were blown wide with desire, and Crowley could see the way his body was moving on top of his own...there could be no doubt what was going on, but Crowley couldn’t believe it. The muscled torso of the hunter got impossibly closer, his mouth coming to his ear and gently saying the demon’s name...

“Crowley...”

The King of Hell started awake in his bed, whipping his head around and reaching for the angel blade under his pillow before realizing he was alone. He forced his breaths to quiet and even out, running a hand over his eyes in annoyance. This was the third time this month he’d dreamed of the Winchester like this...and given this was the third time he’d slept this month, it was worse than he wanted to admit. With his newfound human...ish nature, he’d discovered that sleep was something he occasionally enjoyed, and even needed after particularly stressful or tiring situations. 

It wasn’t as if being attracted to Dean, was any kind of news to him, he’d known that for years. The difference was this new bout of feelings he was having, something a little more out of his control. Demons mainly had lust, not affection, but now he had both. He didn’t think he was in love with the man, but what he felt was definitely more than just friendship, or even wanting to ravish him. And he really wanted to ravish him...

The demon forced himself up, stretching in his silken pajamas a little and looking down at the huge erection wanting to bust free, sighing. He was tempted to take care of it himself, but he didn’t really want to. He wanted a mouth around him, one mouth in particular...his thoughts were interrupted by a knock at his door, and he crossed the elegant bedchamber to open his door, glaring at the demon that stood before him. 

“I believe I said I was not to be disturbed on my day off, save for emergencies. This had better be good.” Crowley muttered, noting with approval that the demon...Antonio, if he remembered correctly, did not grovel or stutter as many did when faced with him, merely bowing respectfully and giving the large bulge Crowley was doing nothing to hide an appraising look. The demon had taken the vessel of a young man, perhaps in his mid twenties, fit and lean, with black hair and copper skin. He kept his hair short, his face clean shaven, and held himself with an almost military poise. Crowley endeavored to find out more about the demon, he liked the look of him. 

“Of course, my lord, I would not disturb you otherwise. We’ve pinpointed the location you asked for, and I hope I was right in assuming you’d want to know immediately.” Antonio said, his hands behind his back, his tone implying he knew Crowley would approve without seeming smug about it. Definitely one to keep his eye on, especially since he’d already made the cut to be on Crowley’s elite team. 

“Is that so? Very well, get me the details and what we have so far. We’ll need to move on this quickly, never know who might be looking for the same thing down here. Make sure the group who knows stays small, and the scouts have limited information. How’s your field work?” Crowley said, surprising the other demon, who’s eyebrows rose.

“Limited, as a demon, my king. Quite extensive in my old life, and I’ve done well with the fighting lessons down here, but that’s not the same as experience topside.” Antonio admitted, not seeming ashamed, just straightforward. Crowley nodded thoughtfully, starting to unbutton his top, sensing Antonio’s eyes on him as he went to his dresser and began to change his clothes. 

“You’ll be coming with me topside, working with humans and an angel, most likely. You have a problem with that?” Crowley said, dropping his pants and revealing his cock which, even half hard, was monstrous. Antonio stared at it without hesitation, then back at his leader’s expectant expression, a glint in his eyes.

“Whatever you want, my lord. You’re the boss.” he said, making Crowley smirk and his dick grow a bit harder...but he forced himself into his clothes, knowing there would be time enough for fun later. Now, there was a Nephilum to save. 

 

_______________________________________________________________________

  
  


Castiel walked down the hall towards Dean’s room, a covered plate in his hands, his grace keeping the food piping hot. He was frustrated that he couldn’t do more for his friend, but not nearly as annoyed as Dean seemed to be at the whole situation. The angel knocked gently on the door, hearing the hunter’s quiet sigh and taking that as an invitation. 

 

“Good morning, Dean. I brought you...breakfast.” Cas said, his expression turning sour when he saw Dean was working on getting himself dressed. He had a tight, black t-shirt on over his bandages, but his pants were hanging loosely in his hand. “Dean, we’ve discussed this. You should give it one more week.”

 

“I’m going stir crazy in here, Cas. You’ve seen how I get when I’m stuck in the  _ bunker  _ for too long, having to stay in my  _ room  _ these past couple weeks has been...I’m running out of all the good stuff on Netflix. I can’t even watch porn for pete’s sake, trying to... _ do _ anything, hurts.” Dean huffed out, looking sadly at his pants for a moment before gingerly holding them out to Cas. “Think I could get some help with these, nurse...?”

 

Castiel sighed, debating how successful he’d be in trying to get Dean back into bed of his own accord. He had a feeling it wouldn’t go well. It had been about three weeks since the whole Michael incident, and though Dean was healing well, there wasn’t anything Cas or anyone else could do to heal the wound caused by the archangel blade. It was beyond him, but healing the good old fashioned way seemed to be going well. Cas went down to his knees as he accepted the pants, giving Dean the best reproachful stare he could, which went unheeded as Dean stuck out his leg and grinned. 

 

“We beat Michael, Dean. You should be grateful for the rest. We have our hands full trying to find out where Nick is, and how to help Jack restore his grace. We got lucky you were only wounded, and that Jack’s soul is mostly intact; we can handle the research while you rest up.” Cas said, working the pants up Dean’s leg and trying not to stare at his crotch. He knew that humans, as a rule, didn’t really appreciate that outside of certain connotations. And as interested as he was to see what weeks without stimulation would do to the human body (of course having  _ nothing  _ to do with who’s body it was, at all), he didn’t think Dean would appreciate the attention.

 

“Owow, easy there tiger. And yeah, I know you guys got this, I just need out. I feel like I’m suffocating in here.” Dean said, sitting on the bed so Cas could finish, his face covered in sweat and his breathing more picked up than the angel would like. It must have showed on his face. “Dealt with pain before, Cas, this is no sweat.” Dean tried, freezing when Cas gently trailed a finger down his damp temple and examined it.

 

“Of course. No sweat. How silly of me to worry. If you’re leaving your room, there are restrictions. No being on your own unless you’re sticking to one spot and are off your feet.  _ No  _ stairs, and no trying to do too much for yourself. And if you want to argue...” Cas said, finishing with the pants and coming up to lean  _ very  _ close to Dean. “Don’t think I won’t put you into a healing coma for two more weeks. I’ve spent too much time tending to you for you to undo all your progress.” 

 

Dean swallowed, and while Cas thought there was a chance it could be fear, he had a feeling it was with something else. If Dean’s pupils were anything to go by. The hunter was so close, it would be so easy to just lean forward and...indulge himself. He was almost certain Dean would reciprocate. But Castiel had promised himself almost a decade ago that he wouldn’t push this, that he would let Dean make the first move, however agonizingly long the hunter was taking. 

 

“Wow, Cas, bossy much? You a nurse, or a drill sergeant?” Dean asked, his voice not quite able to come up with his usual bravado, the words almost hushed. Cas could hear his heartbeat increasing, and was quite sure he could smell Dean’s arousal spiking. But, like always, Cas restrained himself, and gently pulled himself back, holding out a hand for the hunter to help him up. 

 

“I’m an angel, however poor an excuse for one. And if I can’t heal you with my grace, I’ll be damn sure to help you recover the mortal way. Even if it means putting up with your attitude.” Cas said, Dean wincing as he accepted the angel’s help up, keeping hold of his hand for a moment while he centered himself on legs that weren’t used to standing. Dean was essentially leaning on Castiel when the door knocked again, Sam opening it and popping his head in, his eyebrows coming together when he saw Dean up.

 

“Dean, you shouldn’t be...whatever. Listen, mom called, and Washington didn’t pan out. Her and Bobby are heading back. But guess who just showed up with a demon in tow claiming he’s got all the answers to help with Jack?” Sam said, not even blinking at how close Dean and Cas were. At this point, he was desensitized. 

 

“...Crowley? That asshole’s been doing nothing but sending me ‘get better soon’ texts with a gross amount of heart emojis. The hell did he find?” Dean said, his expression getting darker as he tried unsuccessfully to walk out his own door by himself, Cas helping him stay on his feet as a wave of pain hit him. He was pissed with Crowley, mostly because the last time the demon had shown up, he technically  _ had  _ all the answers. And Dean had just laid there with a Gorgon-inflicted head injury while the demon saved the day. 

 

“Woah, easy, you’re not even supposed to be up yet. Come on, stubborn ass, let’s go find out.” Sam said, taking Dean’s other side to help Cas, the two of them slowly supporting Dean down the hall while he tried his best to move on his own. Dean didn’t complain or address the insult, since he was pretty sure he was on thin ice as it was. He’d been a pretty shitty person to live with the last few weeks.

 

“Don’t tell Jack you didn’t eat the eggs, he made them really well today. Only a little shell, you can hardly tell.” Sam muttered before they entered the main library. Dean didn’t say anything, all of his attention focused on not complaining about the massive pain in his stomach, one hand carefully holding at his bandages. Jack was already there, still wearing the chef’s apron Sam had bought him to start teaching him some cooking basics. Crowley was there, impeccably dressed as always, but with someone new beside him. Dean’s first impression was ‘dangerous’. His second was ‘holy shit, this guy’s  _ hot’ _ . Taller than him, but shorter than Sam, he was muscled and dark and had a jawline that Dean wanted to...Dean tried to focus on the pain in his stomach instead.

 

“Finally, I was wondering if you actually wanted to get your Nephilum’s grace back.” Crowley said, looking Dean up and down as Sam and Cas helped the injured hunter into a chair, despite him trying to wave them off. “Well, don’t you look chipper? How goes the wound licking? Castiel doing a good job, I gather?”

 

“You did this to me, asshole. You could at least act a little sorry.” Dean said through gritted teeth, finally opening his eyes to glare at the demon, looking at the king of hell’s attractive lackey and then back at Crowley. “And just because you’ve got a free pass to come and go, doesn’t mean all your little minions do.”

 

“He’ll be assisting us in retrieving what I have high hopes will be the solution to young Jack’s dilemma. As for apologizing, of course you’re right. I’m incredibly sorry for saving the earth, and every human, demon, and creepy crawly creature on it. Terrible of me, I don’t know what I was thinking.” Crowley said, his voice dripping with sarcasm making Dean roll his eyes. Sam cleared his throat, folding his arms. 

 

“What’s this ‘solution’ you keep talking about? We’ve done...a  _ lot  _ of research Crowley, and we’ve been coming up dry.” Sam said, looking at the monumental pile of books on each table in the library. They’d done research for monsters and demons to beat them before, looking for something to heal a supernatural creature was something a little less familiar. 

 

“It’s because you don’t rule hell, Moose. Where else would you find tome after tome of text devoted to our beloved Jack’s dearly departed daddy? Lucifer may not have been the most well liked recently, but I assure you, he used to be rather like that rock star he possessed back in the day, at least to us demons. I had a few of my best and brightest glancing around for anything in regards to places of power or influence related to Lucifer. Most of it is poetic garbage, of course, but we did happen to find one lovely little passage about a church...” Crowley said, walking around the table to Jack, his hands behind his back as he smiled at the boy.

 

“A church? Aren’t those for...god? And angels? Well, good angels...” Jack asked, frowning. He had been getting lots of lessons in between research from both Sam and Cas about the world in general, and from Mary and Bobby when they stopped in from their excursions. But he still knew he had a lot to learn.

 

“Mostly, yes. But a church is a house of worship, and if there were two things Lucifer loved, it was praise, and sticking it to his old man...your grandfather, creator of the universe, all that. So, Lucifer had his followers, the demons, convert a church to the worship of him and him alone. But not just any church.” Crowley said, turning to Sam with dramatic flair. “The  _ first  _ church.”

 

“The first church? Like,  _ ever _ ?” Sam said, having a hard time imagining what such a place would look like. Castiel sighed, folding his arms and leaning against the doorway he was next to. He had never seen it himself, but he had heard about the place from multiple others over the years. It was a memory of shame for the angelic host.

 

“The Dura-Europos Church, in Syria. Demons supposedly tricked the angels guarding the sacred site, banishing them with the help of some human devotees to Lucifer. Through spells of sacrifice and blood, the area became...tainted. Angels can’t approach it, and for many years it was used by his followers to commune with Lucifer, similar to how Azazel did. But it hasn’t been used for such purposes in hundreds of years, we cut off the connection to the Pit once we realized it existed. Angels have ensured no humans who would use it for evil can enter from afar, it’s nothing more than a symbol of our failure. What would the church have to offer?” Castiel questioned, feeling slightly embarrassed to admit the failure of his brethren. 

 

“Well, originally I hadn’t thought it could offer anything. That’s why it was written off as unimportant. But the more I looked into it, the more details I discovered. Those who could most easily commune with Lucifer were those made by him directly. Azazel, for one. Those we know of, Lilith and the Princes of Hell, have all perished...but they were  _ not  _ the only ones made directly by Lucifer himself.” Crowley said, Dean groaning in his chair and pinching the bridge of his nose.

 

“If you’re gonna stand there and tell me we’ve got a whole bunch of other Princes, or Dukes, or freakin Janitors of Hell or some shit to deal with, I’m going to go back to bed.” the hunter complained, Crowley noting the small smile that graced Castiel’s face as the hunter complained.

 

“Thankfully, I believe there is only one ‘Janitor’ that we have to deal with. Antonio, would you care to explain?” Crowley said, the demon nodding, placing his hands behind his back in a military type pose. Dean was loathe to note that his voice was deep, masculine, and authoritative as he spoke...which he hated, of course.

 

“When Lucifer made Lilith and the Princes of Hell, he placed some of his grace inside them. It’s why they’re so much stronger than your average demon, and how Asmodeus was able to gain strength from an archangel’s grace. After he was done with those five, he tried to make more. But he was weakened, and his work suffered. The few he made either died, or were much weaker than the Princes. But one survived, and was tasked with guarding the site of communication with Lucifer centuries ago. We have no record of him being killed, or leaving.” Antonio said, very matter of factly.

 

“So...what, you think he’s still just standing around, waiting for orders from Lucifer or somebody?” Sam said, wondering how that many centuries of boredom would affect a demon. It certainly didn’t sound like much fun. 

 

“Time is different for immortals. Everything I’ve heard and seen from the Princes of Hell makes them seem determined, and purposeful. It wouldn’t surprise me if he stayed at his post, especially if the order came from Lucifer himself.” Castiel mentioned, Crowley nodding in agreement. “But even if he is still there, how could he help us? Even if he could be convinced?”

 

“It will be less a matter of ‘convincing’ and more a matter of ‘slicing his neck open and sucking out his angelic essence’. If my research is correct, as it so often is, it should allow us to extract whatever amount of Lucifer’s grace is inside him. Ideally, it will be enough to return Jack to his previous winged state.” Crowley said, giving the boy a smile. He really was quite handsome, and Crowley wondered if the boy was receiving a proper education...he certainly wouldn’t mind ‘educating’ him himself, but he needed to see just how mature he was first. Body of an adult, mind of...uncertain, as of yet. 

 

“We don’t have time for ‘ideally’, or maybes, or hopefullys. Why can’t you-” Dean started, stopping and shutting his eyes for a moment, breathing out a long breath as Sam and Castiel went to his side. “I’m fine, guys, it’s fine.” he continued after a moment, his face covered in sweat, wincing when Cas started checking his bandages.

 

“You are  _ not  _ fine, you’re tearing your stitches. I told you it was too soon. Now you can walk back to your room with me, or I can carry you, which will it be?” Castiel said, and everyone in the room could see it was not an idle threat. Dean got himself up with some help, Castiel and Jack helping support him as they both walked back towards the bedrooms, Dean not making eye contact with Crowley or his demon lackey. Sam’s shoulders slumped a little and he let out a breath when the three of them were out of view.

 

“Sorry, this hasn’t been easy for him. He hates not being able to do anything.” the hunter said, walking over to and sitting at the table, looking weary. “Honestly, this has taken its toll on all of us. Jack’s fine for now, but we don’t really know how much of his soul is being burned up keeping him alive. Maybes and ideallys are all we’ve got right now. We just want him better.” Sam said, Crowley giving a small smirk and leaning against the table by Sam.

 

“Fatherhood looks good on you, Moose. Even if it is via the world’s strangest adoption. You lot took care of Lucifer, and all of us took down Michael together. Not quite sure where that leaves us, seeing as I rule Hell and all, but I can’t quite bring myself to call us on opposing sides of things anymore.” Crowley admitted. He wouldn’t ever speak like this with Dean, probably not even Castiel, but Sam and he usually had the most common sense and rationality, so talking to him was easier.

 

“I know...for the first time, the world’s not ending, and I don’t know where I stand on the whole Heaven and Hell thing. Demons and angels have both been enemies and...friends, I guess.” Sam said with only a little reluctance, and Crowley was surprised to feel a warmth rush through him. Damn this human emotion to the pits. “But what are you going to  _ do _ ? With Hell?”

 

“Rule it better than any of those other blockheads, for starters. We’re still in the soul business, but with less than a dozen angels flying about, Heaven isn’t exactly the threat it used to be. Everything before was for the grand ‘Celestial War to End All Wars’, and I haven’t exactly been able to do any ruling after all the usurpers. Other than fixing what everyone else broke, I’ve been trying to figure out exactly what demons are supposed to do myself. And not one word of any of this downstairs, understood?” Crowley said, narrowing his eyes at Antonio, who just nodded. 

 

There was silence for a long while, each person in the room contemplating their role in the universe. The playbook had been thrown out with the apocalypse, and there had been one big bad after another since, but now that everyone had time to think, no one was quite sure what to do. What did an angel do, when there was no God to give direction? What did a demon want, when there was no war to fight? 

 

“Don’t suppose you’d consider training all of them to love puppies and bunnies? Maybe go around helping old ladies cross the street?” Sam suggested innocently, Castiel joining them as he spoke. Crowley should his head with a small smile, patting Sam on the shoulder briefly before standing up fully.

 

“Afraid that might be beyond even my considerable abilities, Sam, but I’ll take it into consideration. Sounds like a possible torture method, at the very least. Now, are we going to do this? Or stand around discussing daffodils and roses all day?” Crowley asked, Castiel holding up two bags that the demon knew were just full of all sorts of weapons that spelled bad news for his kind. Perfect.

 

“I told Jack who to call if anything bad happens, and that it’s his job to make sure Dean’s stays in bed. Not quite sure which of us will have the harder task.” Castiel said dryly, wondering why Dean seemed so keen on injuring himself on such a regular basis. He could at least keep it to things Cas could heal quickly.

 

“I’m sure if you were the one staying, Dean would be thrilled to pieces to stay in bed with you, but we’ll need all the muscle we can get.” Crowley said, ignoring the glare sent his way. “Angels and demons both were originally warded away, but with no demons worrying about the area and so few angels, I’m thinking we should be able to get there without too much trouble. Everyone grab hold. Above the waist, if you can restrain yourselves.” 

 

Antonio put his hand on Crowley shoulder, the two others reluctantly grabbing hold in similar places above the waist, and with a small smile and shutting of his eyes, Crowley moved them all across the globe...

  
  


____________________________________________________________________________

  
  
  


“Jack, I get it, Cas put you in charge, but if you offer me chicken soup one more time I’m gonna lose it.” Dean warned, immediately regretting his words when he saw the kid’s crestfallen look. “I’m just not hungry, and in pain, and trapped, all right? Nothing personal, I just get crabby when stuff goes down and I’m sidelined.” he continued, holding his side as he sat on the bed. Jack hesitantly walked over and lifted Dean’s shirt, checking the bandages.

 

“These should be changed...Sam showed me how, when you were unconscious. Can I try? You can tell me if I do something wrong.” Jack offered, and Dean realized there was really nothing else he felt like doing, and this could be the only thing keeping him of dying from boredom. Besides, everyone but him had been teaching the kid lately, he was falling behind. 

 

“Yeah, sure. And...sorry. I know I’ve been a real pain lately, haven’t been any fun to be around. This just sucks. I know stuff’s a lot better, less to worry about, I just hate that I couldn’t...that Michael just...” Dean let the sentence fall apart as he lifted his arms and winced as Jack pulled off his shirt. He’d washed himself up as best as he could before getting dressed, a makeshift bathing station on his side table, but he still had the urge to make sure he didn’t stink. 

 

“I think I understand how you feel. When Lucifer took my grace, I was helpless. Even with some training and everything you guys did for me, it wasn’t the same. Before, it felt like I was this amazing, powerful being that everyone was trying to grab and manipulate, and without my power I was just...nothing. But you guys showed me differently, and even if this doesn’t work...I think I’ll be OK.” Jack said, making Dean’s face burn. Here he was, being a little bitch about some bedrest, and the Son of Satan was overcoming his whole world crashing down around him. 

 

“Oh...I should have...I forgot about the tattoo.” Jack said, making Dean frown in confusion, and jerk a little when Jack placed his hand over the tattoo on Dean’s chest. “I’m essentially human now. Even if it’s temporary, I should have gotten one while I wouldn’t heal from it.” he continued, Dean feeling a small blush creep over him when he realized how odd this situation was. And just how long it had been since anyone had touched him in a way that wasn’t strictly medical. And how warm Jack’s hand was. And how  _ close  _ he was. He moved himself in a way that made a sharp pain hit him to distract himself.

 

“Well, live and learn, right? Now, how about these bandages? We can get a lesson in till the others-”

 

“We’re back!”

 

“...the hell? They were gone for like...twenty minutes!” Dean said incredulously as Sam walked to the door, breathing hard, a vial of glowing grace in his hand. Jack stood up, staring at it in a mix of fear and hope, but Dean just gaped at Sam. “How the hell did you guys do that so quickly?”

 

“It was Crowley! He was right about the wards being down, but then he fed the guy all this bullshit about us trying to bring Lucifer back, and how I was his true vessel, and Cas had been possessed by him too, and the guy could just  _ tell _ ! He totally bought it! He literally offered his neck to Crowley, went on his knees and everything. Guy was devoted, I’ll give him that much.” Sam said with a grin, and Dean just stared open mouthed at his brother, while everyone else caught up and peaked in the doorway.

 

“Well, are we waiting for the boy’s next birthday? Can we see if this will actually work?” Crowley said impatiently, and Sam shot him an annoyed look before walking to Jack. He gently held out the bottle for him, looking him sharply in the eyes.

 

“Hey, even if this doesn’t work, it doesn’t change a thing. You’re one of us, alright? You’re family.” Sam promised, and Jack swallowed and let out a breath. He took the vial, staring down at it for a moment before looking back up and nodding, giving glances to Castiel and Dean as well.

 

“I know. I’m not afraid anymore. And thank you, all of you, for doing this for me. Even if it doesn’t help, it means a lot.” Jack said, his hands shaking slightly when he brought the vial up. He gently uncapped it and brought it closer to himself, closing his eyes and letting his father’s grace rush into him, feeling it travel down inside him and search for his soul. For the first time, Jack felt both his soul and his grace as they came together, but stayed apart. His father’s grace reignited his own, and Jack felt his wings reappearing and spreading out behind him, and he opened his eyes to a room full of awed people. 

 

“...safe to assume that hit the spot, then.” Crowley said, and Jack grinned, turning to Dean and placing a hand over his injured area. Dean made some kind of warning, but Jack ignored it. He felt the wound with his grace, and simply willed it healed, just as it was before, and it was so. A small glow from his hand was all that appeared. Dean’s face look briefly pained, and then surprised, and then ecstatic, and he quickly stood up and started moving about, tearing off the bandages a moment later.

 

“Goddamn, Jack, you got your mojo back!” Dean shouted, and everyone started laughing when he picked Jack up in a big, shirtless bear hug and swung him around. Jack was laughing loudest, and Dean only put him down when Sam put a hand on his shoulder and pointed out how close Jack’s head was to the ceiling. “Thanks kid, feels like it never happened.”

 

“You’re welcome. And...I think my soul is mostly alright. I definitely used some of it, but it feels like more than half is still there...maybe three quarters? Is that...do you think that’s alright?” Jack said, a bit worried, but Castiel placed a hand on his shoulder and smiled, and he felt better immediately.

 

“I think you’re going to be just fine. Tell us if you have any concerns, but if your present attitude is anything to go by, you shouldn’t have to worry about it.” Cas said, and Jack nodded in relief, then looked up at the demons in the doorway. He walked to Crowley, and help out his hand, which the demon took with only a few seconds of hesitation.

 

“Thank you for helping me. I know you did it for them, but I’m very grateful, and...if there’s anything you need, that isn’t evil or hurting anyone, I’d like to help.” Jack said, not realizing every sane person in the room behind him was inwardly screaming at how bad of an idea it was to give Crowley an IOU he could cash in later, especially from a being as powerful as Jack. Crowley, to his credit, merely nodded slowly and held himself back from jumping up and down with glee.

 

“I will keep that in mind, Jack. A pleasure to be of service. Now, I assume you all will want to celebrate, so Antonio and I will just-” 

 

“Slow down there, buddy. Maybe it’s the sudden mobility, or Jack being peachy again, but...it’d be pretty rude to just kick you out right after you helped us. Again.” Dean said, picking up his discarded shirt and giving everyone a lovely show as he put it on. Crowley wondering if Jack considered turning Dean Winchester into the King of Hell’s personal cock sleeve an ‘evil’ action. “Why don’t you stay for a bit, at least for a drink?”

 

Crowley rolled this idea over in his head. He was already socializing with the Winchester’s a lot more than his followers would probably like, but he  _ had  _ been trying to make them understand how different things were with this new regime. And he could always use ‘attempting to get on the Nephilum’s good side’ as a good excuse. He looked at Antonio, who shrugged, but smiled, and Crowley looked back at everyone else.

 

“Why the hell not?”


	3. Apocalyptic Advantages

The text had been unexpected, to say the least. Crowley had invited Dean out for a drink, for “old times sake”, like back when he was a demon. That, and several _very_ suggestive comments, had peaked Dean's interest more than he would care to admit. Crowley had been helping them out a _lot_ lately, practically saving the world in fact, and he wasn't sure what the reason was for it all. He kept thinking the demon had some ulterior motive, but if he did, he couldn't think of what it was. Already had the strongest being in the universe in his good graces, what more did the guy want? That being said, the invite had him thinking about those times back when he wielded the first blade...

 

Even back when he hadn't had a conscience, the two of them had never actually _done_ anything with each other, but they came...close. They fucked a gorgeous set of triplets barely a couple feet apart from one another. Dean was trying too hard to not look at Crowley, focusing on the girls below him and the sensations, but he couldn’t block out Crowley’s sultry voice. Meanwhile, Crowley had no such reservations, and watched Dean’s beautiful, muscled ass drive that gorgeous cock in and out of that sopping, screaming blonde under him. Granted, it was nothing compared to Crowley’s gargantuan prick, but it was a very nice cock. Any porn star would be proud to look and fuck like Dean. 

 

Suffice to say, they had history. History that no matter how he tried, Dean couldn’t shake. Even without all his recent altruism, he probably would have been interested to go drinking with Crowley again. So he went to the damn bar, just told Sam and Cas he needed some tail (which wasn’t untrue, it had been too long), and hoped the demon wasn’t going to screw him over. 

 

He didn’t realize how screwed he was really about to be.

 

It was just like any of the million bars Dean had been inside. Shitty music, shitty beer. Which is why Dean was uncertain why Crowley had invited him here. The demon didn’t really _approve_ of Dean’s taste in atmosphere, but he supposed it may have been Crowley’s attempt at making Dean at home. He spotted the other man at the bar, nursing what was clearly the top shelf that this place had to offer. The sight of the suited shoulders was strangely comforting, somehow, after all the shit that had gone on recently. Dean sighed inwardly as he walked over, and reminded himself that things were changing. Crowley had helped kill Michael and save Lucifer’s son for Pete’s sake. He could have the demon as a...friend. Dean plopped himself on the stool next to Crowley, his shoulders brushing up against him as he leaned over. 

 

“I don’t know if you caught it, Crowley, but you in that suit? Kinda stick out like a sore thumb in this place.” the hunter muttered, peaking around at the rest of the crowd. Denim was everywhere, even a couple cowboy hats. Lots of rough, weathered hands and suntanned skin. Crowley was stronger than any of them, Dean knew, but he certainly didn't look like it with his girly drink and perfect suit. Crowley gave a little smirk and took another sip, before turning to Dean and giving him a considering look. The hunter felt a little exposed, and realized that Crowley looked... _drunk_? Could the king of hell get drunk? 

 

“Well...perhaps you’d prefer I take the suit off, Squirrel? I can think of a couple nuts that would fit beautifully in that pretty mouth of yours.” the demon said, slurring ever so slightly. Now that he could see him better, Crowley's cheeks looked redder than Dean had ever seen them. How much had he drank? Dean recoiled a little from the leering gaze, but not too much, wanting to keep this conversation private. The men in the stools behind him were close enough to overhear if they tried to. 

 

“Are you fricken serious? You called me out here, for...what, a bootycall? Drunken pity party? I drove for nearly an hour! Up yours, Crowley.” Dean said, getting up, gasping as Crowley’s hand flew up and grabbed a fistful of his shirt, yanking him back down against the counter with demonic strength. Dean barely managed to keep his head from slamming into the counter, but Crowley kept him pinned with what seemed to be little effort. 

 

“There’s that smart mouth of yours, always getting you into trouble. Did you ever stop to think that perhaps you _aren't_ the most important person in the room, that some of us have a literal HELL to run? No. No you have not.” Crowley said, quietly muttering in Dean’s ear and making the other man shiver. Crowley’s tone was measured, calm, and dangerous. Dean kept quiet, a chill running up his spine and down to his toes. This wasn't what he expected. Or maybe it was. Maybe this was why he came out. Crowley had been a lot more crass than usual over text, but Dean had chocked that up to nerves, or the demon covering something up. He was starting to think he _may_ have been wrong. 

 

The demon chuckled and Dean could smell the expensive alcohol on his breath, feel another hand creeping around his belt, making him squirm and get red in the face. Too late, he realized Crowley wasn't copping a feel, and the angel blade he’d brought was removed before he could fight for it. Dean couldn’t tell what was done with it with his head and body pulled flush with the counter. 

 

“And here I was hoping you’d be more pleased to see me. After all, I’ve given so very much for you boys. Helping to remove Michael, saving your beloved Jack. And what have the Winchester’s given me in return? Besides some sub par drinks? Multiple dethronings, several close calls with death, and rather tight pants.” Crowley hummed, leaning down and putting his lips close to the hunter’s ear. “That last bit was your fault, personally. Do you have any idea how hard it’s been not to take you? Not to desecrate your sinful body because you and your damned angel can’t get to it fast enough? Do you know how hard you get me? How much I want those plump lips absolutely stretched around my colossal cock?”

 

Dean’s entire body gave a huge shudder at Crowley’s words, his mouth opening and closing like a fish while he tried to find words, ANY words, just to make Crowley stop talking. Because his cock was growing in his pants, and in the name of all that was unholy, he could not let Crowley find out what this was doing to him. Or about the maybe, sort of crush he had on the older demon. Which he may have stamped down with the rest of his demon memories as best he could. Crowley’s other hand pressed something hard against the small of his back, and slid down, slowly pressing along Dean’s ass and making the hunter squirm against the counter, trying to free himself. Why wasn’t anyone screaming? Or saying anything? All the noises around him told him the bar was busy and...normal, but what Crowley was doing was NOT subtle.

 

“Now now, Dean. It’s not good manners to refuse a gift from a friend. So just let me give it to you.” Crowley said, expertly flipping around the angel blade and slicing the back of Dean’s pants in one fluid motion, from just blow the belt to where it stopped between his legs, exposing Dean’s whole crack and balls to Crowley and anyone else who was looking. Why was no one else looking? Dean was struggling now, trying to shove and kick, but Crowley had a strong grip on his shirt, and none of Dean’s glancing blows so much as made the demon flinch. It did make a nice breeze on his ass, and all of Dean’s considerable willpower did nothing to stop his cock from becoming fully erect in his ruined pants.

 

“Oh, that _is_ a sight...I told you, didn’t I? Finest ass I’ve ever seen.” Crowley said, and Dean’s face paled when he realized the demon wasn’t talking to him. Three different men agreed, calling Crowley “sir” and “my lord”, and Dean slowly skunk down on the counter, stopping his resistance. Demons. Every person inside this bar was a demon. And all of them were men, now that Dean bothered to look around. And everyone he could see was staring at his ass and talking amongst themselves. Several of them seemed to be adjusting themselves in their jeans, and Dean gulped before he was flung back into the crowd of three behind him. 

 

“I don’t think the bar will do. Somewhere a little more central, a little more...poetic. That’s how you made a living, isn’t is Squirrel? Hustling men at pool, playing with sticks and balls till you got what you needed? Right there, the one in the center.” Crowley directed, and no matter how much he fought and struggled, the demons’ grip was iron. His heart was beating out of his chest, fantasies he had kept locked and sealed shut in the deepest parts of his mind pounding and trying to get out. He was grateful Jack had healed his stab wound a couple days prior, but a hell of a lot of good it did him now. 

 

He thought they were going to bend him over the table, but he was wrong. They pulled him up and on top of it, kicking his legs till he was on his knees, upright but spread more than he would like, his ass on perfect display for anyone behind him. Crowley made his way in front of him, right at the edge of the table. Close enough to spit at, but Dean didn’t want to risk what would happy if Crowley was angry _and_ horny. The demon looked at him for a moment, a small smile on his face. 

 

“You know, Dean. You still haven’t actually told me ‘no’.”

 

Dean blanched, looking down at Crowley with a sneer. He hadn't, technically, but he thought it was implied with all the kicking. A very small voice in Dean's mind said there was a reason he hadn't quite managed the simple word out, that he wanted to see where this went, but he ignored it.

 

“You think I _want_ this, dickwad? The hell is wrong with you?” Dean nearly shouted, wanting to make sure everyone heard him. The smirk Crowley gave was nothing short of victorious, and Dean’s belt undid itself without any hands touching it. The hunter felt his face redden even more than it was already, and looked up and away in shame as Crowley unzipped his jeans and gently slid down his boxers, revealing Dean’s cock. Eight full, thick inches. Hard as steel. Literally dripping more precum than it had in the last decade. Crowley gave it a little flick, making Dean wince, but he couldn't look at it, couldn't see his own body betray him like this. 

 

“And what, pray tell, do you call that?” the demon said quietly, half distracted by the beautiful sight before him. He was certain Dean would enjoy this after a time, but he hadn’t expected him to be quite THIS pleased with the situation. The diamond rod in front of him throbbed as he addressed it, and Crowley grinned, realizing how desperate Dean must be.  He was half tempted to swallow the hunter down right here, his hung friend clearly in need of relief. His fantasies about the hunter had grown more and more demanding during his time fixing Hell, but he was starting to think he hadn't been the only one thinking about this. But this was a lesson for Dean, his punishment for putting Crowley off for so long, for making him wait. 

 

“It’s nothing.” Dean said quietly, and swallowed as several demons let out hissing and poorly concealed laughter. Crowley silenced them with a wave of his hand, taking Dean in his hand and giving him a slow stroke, Dean’s body starting to shake with the conflict between pleasure and keeping up his image. He wanted this, he wanted it so bad, it was actually scaring him. He was supposed to keep this all in his head, how had Crowley _known_?  

 

“This, is not nothing. It’s a beautiful cock, worthy even of the King of Hell.” Crowley said, licking his lips. He wanted to make the hunter feel good, to show him what a fine piece of...art, he was, and how much Crowley could do for him. He shook his head sadly, tutting. “But I have something else in mind today. And I think you know what it is. You can either give it to me, or I can take it. And I think you know which one you truly want...truly need.” 

 

Dean froze, finally looking down at his...frenemy, who was staring up into his eyes with glee as he gently ran his hand up and down his shaft. Crowley was asking him his permission? Dean looked around at the room, filled with multiple horny looking demons, with a sharp retort on his tongue. His eyes found a familiar face in the crowd. Antonio, approaching the pool table with a smile on his face, and he hesitated, no words leaving his mouth. 

 

“You should also know, if you deny me, there will be no secrets kept by any in this room. Many witnesses to spread the word on just how much Dean Winchester likes a little 'rough play'. And you _do_ have appearances to keep up. And what will poor Sammy think if he starts getting dozens of texts a day, asking when his big brother can come out and play? Perhaps Castiel will get some unusual and perverted messages over facebook, he's still so new to the social media scene.” Crowley said, sending his thoughts racing. Crowley didn’t stop stroking his cock, and Dean closed his eyes and bit back a whimper when the demon played with his slit, rubbing his thumb gently over it repeatedly. 

 

"If I say yes...this stays a secret? No one's gonna know?" he said, his breath coming out in pants, and Crowley hummed in agreement. “And it'll just...just be you? Once?” Dean asked, opening his eyes and pleading with Crowley without speaking, his eyes glassy and desperate. The king of hell couldn't believe this was so easy. He had underestimated the lifetime of repression and desire warring with desire inside the man, the very thought of this type of situation prompting many of the hunter's one night stands, just so he could keep up his image, even to himself. 

 

“For now. I don’t think you’ll be able to last more than a few weeks without coming back for more, but you did survive hell for quite some time. Stranger things have happened. But tonight? I will satisfy myself with one round.” Crowley said, sighing wistfully. He could easily go a dozen rounds with the Winchester, but this was Dean's first time, and he was being so wonderfully compliant. Maybe it was all his helpfulness recently, maybe it was how long the hunter had been stuck in bed with no one to really take care of him. Crowley didn't really care, his eyes traveling over the beautiful revealed parts of his friend's body. 

 

Dean tried to reason another way around this, another way out. He believed Crowley would let him go, if he really asked, really reached out...but the truth was pretty plain. Not once during all this had his erection flagged, he couldn’t stop dripping and shivering, and all Crowley was doing was giving him a lazy handjob. He wanted the King of Hell, had wanted him long before he’d been a demon, and this was exactly the fucked up situation he’d dreamed Crowley would subject him to. Not during their first time, granted, but still. Finally, Dean nodded, breathing out a single, shaky, “OK.”

 

Crowley smiled, letting go of Dean and slipping off his suit jacked. The hunter’s cock throbbed when Crowley rolled up his sleeves, his body eagerly betraying him at the thought of what was to come. Crowley snapped his fingers, and after a brief moment the hunter yelped as a cold, lubed set of fingers went right to his ass and prodded at his hole, Dean trying to close his legs despite the demon’s iron strength keeping them apart. Crowley was lifted on top of the table, and Dean shuddered as the henchmen’s fingers started to roughly try to insert themselves. He looked back, and Antonio was crouched behind him, his long fingers playing with his virgin hole.

 

“Y-you said it would just be you! Aah!” Dean cried as Antonio finally gave up on trying to shove several in and slid his middle finger in as deep as it could go, making Dean’s cock jump and actually shoot out a bit of pre. It hurt, but his body was on fire, finally getting what it had craved for so many years, and the pain went straight to his cock. Crowley chuckled at Dean's reaction as he unbuttoned his perfectly pressed pants and revealed beautiful silken boxers the color of blood. Dean’s jaw dropped at the size of the demon’s bulge. This had to be a joke, right? No ones cock was that big. 

 

“He’s not having sex with you, Dean, as much as he might want to. He’s just helping you get ready. And believe me, you’re going to need all the help you can get.” Crowley promised, whipping out a weapon that was, in no uncertain terms, a foot long, and as thick as Dean’s closed fist. Dean’s mouth just gaped, and he heard the demons around him speaking, making lewd comments, a couple of them patting him on the shoulders and back in mock wishes of good luck. Or maybe they were genuine, maybe a cock that size caused even demons to feel pity. 

 

“...you’ll kill me. That...that thing will tear me apart. I can’t take that, I’m a-“ Dean stopped, hesitant to use the word to describe himself. Crowley was bigger than anything Dean had seen, and he had watched a _lot_ of porn. Antonio slid in another finger, and Dean squeezed his eyes shut as pain and pleasure surged through him, and he heard Antonio hum in approval at his reaction. He let out a strangled cry as the fingers stopped thrusting to explore a little, brushing areas that had never been touched, making Dean's legs shake. 

 

“A virgin? Yes, I suppose you are. Which means you’re going to be incredibly tight...I’m going to enjoy this Dean, very much. But I want your other hole first, and, I am sorry, but I’m not going to stop until you’ve taken as much as you physically can. Don’t worry, I’ll use a little 'demonic influence' to make sure you don’t get... _too_ damaged. Perks of being king.” 

 

With that, Crowley stepped forward, his followers chattering excitedly as their king grabbed the feared hunter’s head and began to shove at his closed mouth with his dick, smearing the start of a large puddle of pre that would soon begin to cover Dean’s face. The hunter tried to fight it, but Crowley was too strong, and every inhale just brought more of the demon’s intoxicating musk to his senses. Dean wanted so badly just to open up and taste, to try, to swallow and suck his first cock and enjoy himself, but he couldn’t with all these demons around. None of them would ever fear the Winchester name again if he didn’t at least try to fight. 

 

The third finger is what did it. Antonio punched in a third finger roughly, and Dean had to open his mouth to yell. Three thick inches slipped passed Dean’s lips and were only stopped by Dean’s automatic attempt to bite down on the invader. Infuriatingly, Crowley’s dick was as strong as the rest of him, and all the demon did was gently slap Dean’s cheek a few times, smiling down at the fear in the other man's eyes. 

 

“Now now, Dean. Very naughty. Be a good boy and swallow daddy’s big cock. Unless you think you’re ready to take it in your other hole now?” Crowley said, and Dean froze. The taste of Crowley’s clean cock and delicious pre, the feeling of fingers other than his own stretching him and sometimes hitting than spot in him...it was all driving him crazy with want. He wasn’t ready to get fucked by Crowley, there’s no way that would feel good right now, and he felt a tear roll down his face when he realized just how much he wanted it to feel good. He didn’t start sucking...but Dean stopped resisting Crowley’s cock, letting a couple more inches slide in before his gag reflex kicked in and squeezed around the demon’s dick. He tried to cough, but Crowley didn't push forward, letting Dean try to adjust to the huge insertion. 

 

"Such a good boy...you've wanted this even longer than I've wanted you, haven't you? Needed a strong man in your life, to take a little control out of the hands of the world-saver." Crowley murmured, keeping his voice low. A few demons would hear, but this was between him and Dean, public humiliation aside. Keeping on gentle hand on the back of Dean's head, he slid a few inches out, then back in, repeating the motion as he felt Dean's mouth begin to fill will saliva and slick his passage. The hunter was trying his best to stay quiet, but the combination of Crowley's words, prick, and those damn fingers in his ass working him open were forcing needy little moans from his throat. The sounds he was making were starting to break Crowley. 

 

“Yes, Dean, that’s it. Let me use you, just let me teach you a little lesson, hmm? About respect? About where exactly this relationship will be going?” Crowley grunted, speaking louder, gripping the back of the hunter's head harder and pulling him onto nearly half his cock. Dean choking and gagging as his lips were stretched around the giant prick was driving Crowley insane, but the best part was the desperation. Every time it was almost too much for Dean, Crowley would pull back and let him breath. But once he had enough air, Dean would open his mouth and stick out his tongue eagerly, his cock and mouth drooling almost in tandem, and Crowley would slide back in. Their eyes were locked much of the time, Crowley wanting to see the mixture of hate, lust, and gratitude in Dean’s eyes as he finally got what he needed so desperately. A huge cock stuffing his throat. 

 

About ten minutes passed of words of praise and humiliation from Crowley, choking, gagging, and moaning sounds from Dean, and quiet laughs and jokes aimed at the eager cockslut hunter from the various demons watching and touching themselves. Crowley realized he would cum very soon if he kept using Dean's mouth, and as tempting as it was to see Dean try to swallow the flood he was preparing to unleash, Crowley really wanted to get into that other hole.  With that thought, Crowley put both hands on either side of Dean’s head and shoved, a full eight inches of his monster cock slamming into the hunter’s gullet. Dean’s eyes bugged out, his air cut off and more meat stretching his throat than he thought possible, and he made what little pleading noises he could around Crowley’s fuckstick. But the demon was busy throwing his head back and shouting, enraptured in the feeling of the hunter's throat trying to squeeze and remove him and failing.

 

“Lucifer, YES! This, THIS is what you were made for, Dean!” Crowley cried, finally letting his cock slide out as Dean doubled over and coughed, breathing in needed lungful’s of air. “Taking the cocks of your superiors, and loving every second of it. Antonio, is he ready back there? I need to get balls deep in something, and he can’t take me all the way down his throat yet.” Crowley asked, the other demon smiling up at him and nodding as he removed all four fingers from deep inside the hunter. Dean’s breathing was ragged, but evening out, as Crowley used his fingers to lift his chin and look him in the eyes, wiping the tears from the hunter’s face. 

 

“We are going to have a so much more fun in the future, you and I, I have no doubt. Once you get over the shock of tonight and let yourself accept the truth. But you’ve made me wait too long, and I can’t be patient anymore. Not tonight. So I apologize for any undue pain, but I’m going to have to make you my whore tonight. Do you understand, Squirrel?”

 

Dean was silent for a moment, swallowing once and feeling the taste of Crowley on his lips. 

 

“Gimme everything you got, bitch.” Dean said quietly, trying and failing to put any challenge in his voice, his eyes glazed as a tired but blissful smirk came over his face.

 

Crowley realized this was the closed thing he would get to Dean begging him to fuck him with everything he had. The king of hell smiled, almost warmly, and kissed the hunter on the forehead. Dean closed his eyes, knowing what he just asked for might actually break him, and not caring. His blood was boiling; he _needed_ this, in a way he had never needed anything in his life. His cock was red and aching from being neglected for so long, the choking and fingering having made it harder instead of making it wilt.

 

Crowley's demons went to either side of the hunter, the hands keeping Dean in place hardly restraining him so much as supporting him, but now they lowered Dean onto all fours as their leader knelt behind him. Crowley lowered his garments to his thighs with one hand, stroking his massive, lubed prick with the other while his demons made quick work of the Winchester's pants. Crowley wanted to make the sound of his balls slapping Dean's ass to be heard through the whole bar, and he grinned when he saw what a wet little thing Dean's nearly virgin hole was now. 

 

"Well done, Antonio. You'll be first in line whenever Dean begs for a dick to fill whatever hole I'm not inside of. You even cleaned it out for me...how thoughtful." Crowley praised, the demon lowering his head in submission, but couldn't keep the grin off his face at the idea of debasing the Winchester further in the future. Dean's arms were shaking as he waited, tears coming into his eyes. The demons were barely holding him, he knew he could run if he wanted to. He might even be able to get away, he'd run from plenty of monsters before, and he still had his shoes on. But this was something he couldn't bring himself to run from, even though he knew pain was coming. 

 

"Now, Dean, I know you spent quite a bit of time below, but this pain is going to be different than anything down there. I'm sure you know that. I'm about to violate the most intimate part of you, and it's going to...we'll go with 'sting'. But since you're giving us such a good show, and you've been such a good little slut for me tonight, I want you to tap out if you need me to go a bit easy. I expect you to put up with the pain as best you can, be a good little trooper, got it? Emergency use only." Crowley said, gently caressing the man's ass with his fingers, watching him shiver a bit before finally nodding, keeping his head down and not trusting himself to speak. 

 

Crowley gently slid in a finger, testing the waters, and Dean gave an involuntary little moan as the digit slid in easily. It would be easier if he used a dildo on the other man, or even let another demon or two go first, but he needed to be the first one to penetrate his gorgeous friend. Removing his finger, he moved himself into position, putting the blunt head at Dean's entrance and giving a gentle push, a shudder working it's way through the hunter's body as his hole tried to resist the huge missile. 

 

"Deep breath, love." Crowley ordered quietly, and he felt Dean breathe inward as he pushed a bit harder, a hand gripping his cock, the other on his whore's hip. The demon was an expert at how the human body worked, especially when it came to sex, and the head of his cock popped inside just as Dean's lungs were full of air. Which meant the yell of pain and pleasure that came out when he was breached was loud enough that the demons let out a raucous cheer to match, several of them patting Dean on the shoulder and back, a gesture that would have humiliated the man if he'd been able to think rationally. Instead, he whined and raised his head a little so he could breathe easier, and Crowley rubbed his own hand across Dean's back comfortingly. "There now, only eleven inches to go."

 

 _Oh my god, he's going to shove that whole thing in me. He's going to be balls deep, I'm going to take all of_ \- Dean's thoughts were spiraling, and he gripped at the edge of the table to try to stop them. He could feel his entire body turning red with embarrassment and arousal.  _Don’t cum, do not cum, he's barely even in me, please don't shoot too fast, I'll never live it down._

 

Dean's thoughts were interrupted as Crowley started to push forwards slightly, his cock slicked with lube and too hard to allow for much resistance. His mouth opened as one, then two inches slid into him, stretching him as much as those four fingers had like it was nothing. He hissed and threw his hand back to push Crowley's hip and stop him from going further as that fourth inch hit, but Crowley merely grabbed it by the wrist and twisted it so it rested just above Dean's ass, a guttural moan escaping Dean as another inch slid home and caused him to start losing control. 

 

"I told you, emergencies only. You're not even halfway there yet." Crowley admonished, and Dean cried out in pleasure and pain as Crowley paused for a small second before punching in another inch, ending Dean's resistance. "There, now you're halfwa-" Crowley started before Dean's screams and clenching hole cut him off and made him realize the other man was beginning to orgasm. Spunk began to shoot out of his prick harder than Dean had ever experienced, his clenching hole forcing his orgasm to keep going. Demons watched in awe as every muscle in the Adonis-like body of the Winchester tensed and flexed as spurt after spurt of cum shot all over the table, several demons, and absolutely coated Dean's own pecs and stomach. 

 

Crowley just gaped as the Winchester fell apart under him, absolutely beautiful in his humiliation and pleasure. Demons, even Antonio, shouted encouragements to the hunter as he lost himself in his own pleasure. As his orgasm finally died down, Crowley released the wrist he was holding, allowing the man to slide off his cock and collapse in a sobbing pile of sweat and semen. The demon's pricked was angry red, his annoyance at being interrupted before he really started sated by the expression on Dean's face as he turned onto his side, almost looking surprised and shocked at what had just occurred. Crowley started unbuttoning his vest, then his shirt, Dean slowly focusing on him as Crowley revealed a slightly hairy, tattooed torso that had both pudge and muscle. Dean's eyes traveled over him hungrily, making the demon smile. 

 

"Spread him for me. It's my turn to get some relief, wouldn't you agree?" Crowley asked as he finished unbuttoning, Dean letting out a loud groan before the demons grabbed his legs, lifting them into the air and spreading Dean's hole wide for their king. Dean panted, not resisting, but grabbing onto the thighs of the two demons holding him and clinging like he was going to drown. Given the load boiling inside Crowley's balls, that wasn't outside the realm of possibility. Taking his cock in hand, the demon slid it across the hunter's hole several times before sinking in with a groan. 

 

Dean's cock had been shrinking down after his orgasm, but the demon king's dick sliding up into him as Crowley gripped his flagging erection and stroked forced a strangled groan out of his lips and brought his cock back to hardness before Crowley had sunk halfway in again. He hadn't been this responsive in over a decade, his mind just as desperate for more as his body. For a few gentle thrusts, Crowley stayed where he had been before, then both hands gripped Dean's thighs, and he began to work himself deeper inside the hunter despite Dean's halfhearted protests.

 

"It won't fit...oh god Crowley, _please_ . You're gonna split me, _please_ ease up." Dean whimpered as his virginity was slowly fucked away, all sense of pride ripped away with his first orgasm. Crowley's demonic powers were the only thing keeping him uninjured, though Dean didn't know it. No guy could take a dick this big his first time without significantly more work than what he'd been put through. But Crowley wasn't willing to wait, his patience had run out. Dean had already gotten off, and while Crowley was certain he could do so again, that was...less important now. 

 

"I'm going to fill you up so much, little hunter. You have no idea how long I've waited for this." Crowley crooned, nine inches of his dick sliding almost all the way out before being mercilessly pushed back inside Dean's ass, the poor man crying out in ecstasy every time he was fucked deep. He was getting worked up again, finally breaking and letting go of the henchman's leg to start stroking his cock in time with Crowley's thrusts, needing to cum again. "And this won't be the last time, you know it won't. We'll keep the secret up here, but everyone down in Hell will be happy to know one of the Winchesters has been turned into a proper slut in need of a good breeding on a daily basis. Think you're ready for the rest?"

 

Crowley didn't wait for an answer, leaning down over the younger man, supporting himself with his arms and starting to piston his mammoth cock in and out at a brutal pace, working himself deeper with every thrust. Dean began to cry out in rhythm with Crowley's thrusts as he looked up into the demon's eyes, the fucking harder than Crowley had gone before, all gentleness gone. Every fiber of his being wanted Crowley to come down those last few inches and kiss him, but he couldn't make himself ask, even if he'd been able to speak instead of shout. He felt his orgasm start to rise, but Crowley was too smart for him, grabbing the hand stroking his dick and pinning it above his head, bringing the other up to join it, pinning his arms above him with the demon's weight as Crowley felt himself sink in just a little bit more. 

 

The demons had been encouraging before, but that increased into cheers and even some applause as the sound of balls slapping ass started to sound in time with Dean's cries, the king of hell finally fitting every inch of his monster cock inside the Winchester's ruined hole. Crowley took that encouragement as a sign and began to truly plow the other man, showing him just how much he'd been holding back, just how hard the demon could fuck him. Dean's teeth were gritted, his body stretched to the limit as Crowley's constant hammering of his insides kept his orgasm so close, but just out of reach. Crowley was grunting like an animal now, getting louder and louder as he slammed himself again and again inside the hunter's hole, Dean just hanging on as his friend chased his orgasm. 

 

"Come on Crowley, fill me up, holy _shit_ you feel so good..." Dean whispered up to him desperately, hoping Crowley would take pity on him and let him cum. The demon grinned and kept up his brutal pace, panting and clearly enjoying himself more than Dean had ever seen. 

 

"Louder!" Crowley said with a grunt, shifting his position slightly, making Dean's eyes widen and jaw drop as the demon king began hammering right into his prostate, almost sending him into orgasm, but not quite. 

 

"Fuck yes, just like that! Oh god Crowley, fuck me, please don't stop! I'm so close, oh son of a _bitch_! Please, please, pleasepleaseplease-" Dean's words were cut off as he felt the impossible happen, the demon cock in him started to swell even bigger than before, Crowley's balls drawing up close to his body as his orgasm neared. Not for one second did Crowley stop thrusting, every thrust harder and deeper than the last as his control left him and his eyes flashed crimson. 

 

Dean came hands free again, his sweat soaked body arching off the table and his face contorting as he finally achieved agonizing satisfaction, his voice only drowned out by Crowley's animalistic screams as every inch of Dean's insides was coated with demon spunk. The demon kept both their orgasms going for over a minute with his unstoppable thrusting as he worked close to a gallon of cum inside of Dean's hole, Crowley's power keeping all of it inside. The king of hell finally stopped, sliding himself up and panting, but grinning in total bliss. His eyes ran over Dean, who was totally covered in his own release and sweat, and breathing so hard it looked like he might pass out. He looked breathtaking, and Crowley resolved that this would be something that occurred on a regular basis. Maybe without the audience, so he could show Dean he could take as well as give. He leaned back over the man, putting a hand around his neck and forcing him to look at him.

 

"Now, before anything else. What did you just beg me to do?" Crowley said, his breathing almost normal while Dean's was still ragged. The hunter had to work to focus on the question, and that small, shattered part of him in the corner of his mind told him to spit. To fight, to defend his pride. Or at least to refuse to answer.

 

"To...fuck me. And not to stop." Dean said, his voice hoarse and broken. Crowley knew it was loud enough, that his demons could hear, and he gently wiped the sweat from his friend's forehead. "And to cum inside me..." Dean finished, tears in his eyes, but he didn't let them fall. Crowley nodded, pressing a kiss to the hunter's lips, who only took a few seconds before returning the gesture. It only lasted a moment before the demon pulled back, but Dean let his body slump onto the table, defeated. He hadn't held anything back from Crowley now.

 

"And don't you forget it. I know how you work, I know you'll try to justify this in your head, deny it happened like I said, whatever you have to do. But at the end of the night, my lovely little Squirrel, you absolutely begged for it. Remember that, I don't want to have to wait long to do this again. Understand?" Crowley said, buttoning up his shirt and vest but leaving his huge, dripping cock out. Dean's eyes kept flicking to it, unable to believe he had taken it all...and wondering if ( _when_ , if he was being honest) it would happen again, before nodding. "Alright you lot, get him some food, water, and a pair of pants. Any good athlete needs to be taken good care of...and I'd say our hunter just knocked it out of the park."

 

Demons rushed to listen to their leader, helping Dean gently off the table, holding him up while they worked a donated pair of jeans onto him, someone grabbing his belongings from the old pair. They left him shirtless, many of the demon-possessed men working weathered hands over him with excuses of massaging or checking for injuries, and Dean shivered. He was in a haze, and their touches felt like a mixture of disgusting and pleasant. Which is how Dean's whole body felt, if he was being honest. He could feel the cum Crowley had pumped into him, and it wasn't coming out, which he supposed was one small blessing. One of the only demons who didn't touch him was Antonio, who just kept staring at him. 

 

He was carefully seated at a table, given a huge glass of water and a cold beer. He just stared at both for almost a minute before Antonio sat with him, held the glass up to his lips, and made him drink. He gulped it down obediently, his throat sore and dry from the mix of fucking and shouting. Antonio had the glass refilled, demons listening to his quiet commands, and had Dean drink again. The hunter was very out of it, but it seemed like most of the demons were piling out. Where they were going, Dean didn't know, but he was certainly getting a lot of winks and waves as they left. He stared at the table, his shoulder slumped and head hung in shame. 

 

"Now now, I won't have you looking like that. Not after the fun we just had." Crowley said, immaculately dressed and looking like he hadn't just fucked Dean's ass six ways to Sunday. He sat down next to him as the remaining demons disappeared, all save Antonio, and leaned close to him. "I know you're going to start spiraling into guilt and self loathing and whatever else happens when you Winchesters let yourselves enjoy anything, so I've given you some options." he continued, handing a numb Dean his phone, which was already lit up with a prepared text message. "This is telling Sam you've popped off to work a small haunting, nothing to worry about, you'll be home in no time. If you want some time to yourself, that is. There's a motel within walking distance, if you don't feel up to driving, as well."

 

"Option number two, I have some demons that have gone a bit...off the rails. Not quite going along with the New Hell motif. Murdering up and down the coastline without anyone's say so, for kicks. I was going to punish them myself, but if you need to work out some aggression on something you don't have to feel guilt over, well..." the demon king offered, taking Dean's silent staring at the phone as a no. "Third option is to drive home, go to bed, and see how you feel in the morning." Surprisingly, Dean nodded at that option, still not saying a word. Crowley nodded in return. 

 

"Very well. Do you feel like me or someone else taking you, or would you prefer to drive yourself? I can have one of my men drive your car if you-" Dean was shaking his head firmly, snapping a little out of his fog at the thought of a demon behind the wheel. "No to demonic Uber, then. Well, in that case, I'm afraid we have one more thing to do." he continued, sliding his hand over and onto Dean's stomach, making the Winchester swallow and jerk slightly. "You have got one, very large load of mine inside you, and the second I leave, it's going to come spilling out of you."

 

Dean stood up quickly, wincing as his sore muscles protested, and looked around for the bathroom, as Crowley pulled a shiny gold item out of his coat pocket. Dean stared at what was clearly some kind of buttplug, but it looked...mystical, with runes and other symbols etched around it.

 

"No bathroom here, I'm afraid. Chose this place carefully. You can go outside, if you'd like, but I doubt you'd be able to keep those pants clean. But this? This will keep my cum nice and sealed inside you till you get home, and fix any damage I may have caused as well. You're very stretched right now, Dean, and I can't promise there won't be any accidents on the way home if you try to go without it." Crowley said, walking closer to Dean, who was close to his limit. His voice shook as he spoke, forcing himself not to cry.

 

"Why, Crowley? Why are you doing this? I don't...I don't get it, I thought we were friends now. Or that at least you were less of an ass than you used to be. You've been _helping_ us." Dean protested, not resisting when Crowley put a hand on the back of his neck, squeezing comfortingly. The gesture felt grounding, and Dean hated how nice it felt. He didn't know what he was going to tell Sam, or Cas...or if he was going to say anything at all.

 

"Don't act like I didn't just give you everything your perverted little heart desires, Dean. I'm very good at knowing what people want, and you're no exception." Crowley murmured, leaning his face in close and letting his voice become chastising. "And you're the one who made me wait. When you were a demon...sweet Lucifer, can you imagine the fun we could have had, if you'd pulled your head out of your ass? Days, Dean, we could have gone on fucking each other like rabbits for _days_. I couldn't wait any longer. And good luck trying to convince anyone those weren't your two best orgasms. Which one was better, the one where you were bent over? Or the one where my men held up your legs, so I could really get myself good and deep?" Crowley whispered, squeezing the back of Dean's neck as the hunter stared wordlessly at the floor. He stayed still for a solid two minutes, warring with himself before he slowly undid his new jeans. Crowley hummed in approval as Dean slid them down to his knees, turned around, and bent over the bar. 

 

"There now, see? Was that so hard? This shouldn't hurt, the whole point is to heal you." Crowley reassured him, but Dean still tensed when the metal pressed against his tender hole. Thankfully, Crowley was right, the metal hummed slightly as it began its work, and Crowley pushed it past Dean's defenses without any pain. Dean groaned as the thing settled within him, and his cock gave a valiant twitch. The king of hell's hand gently started stroking it, the plug humming inside him and making him start to get hard again, but Dean turned and gripped Crowley's hand.

 

"Please, I can't...no more tonight, OK?" Dean pleaded, looking wrecked and shaky. Crowley smirked when he heard 'tonight', and nodded, but pulled Dean in for a kiss. The hunter almost fought him. Almost. Before sinking into the kiss with a tired groan, barely able to participate, letting Crowley's tongue explore him for a few minutes before the demon pulled away. "Can I...can I go home now?"

 

"Yes, Dean, you've been very good for me. Go get some sleep." Crowley said, giving the hunter one more kiss on the forehead and letting him walk away, knowing there was no way in hell Dean would be able to stay away from him for long after tonight. Dean slowly walked out into the night air, taking a few deep breaths as he felt the gently humming plug shift inside him. It was making him feel better, he realized. Less sore, less exhausted, but Dean still needed sleep desperately. Without looking back, he wearily walked over to the Impala, grateful for such a familiar sight. Tomorrow, thinking about this could wait until tomorrow. 

 

Antonio came over to stand by his king as they watched the Impala roar to life, Crowley wearing a soft smile. He could still feel the lube on his fingers from being inside the hunter's ass, an experience he couldn't wait to repeat.

 

"You aren't afraid he'll fall asleep at the wheel?" Antonio asked, frowning as Dean drove off. It would be a shame for the slut to die before he had a chance to do anything more than prep him. 

 

"The Winchesters live their lives in a constant state of exhaustion. Coming home from hunts, burying loved ones, crossing the entire country by car. They're quite used to driving at night, even while in a state of near collapse." Crowley said confidently as the tail lights disappeared into the darkness. "That, and I spelled the plug to vibrate intensely if Dean falls asleep while wearing it. You know..." Crowley said, smirking as he turned off the lights in the building with a snap of his fingers. "For safety reasons."

 


	4. Adjusting and Unexpected Lessons

**Summary for the Chapter:**

> Dean adjusts to life after his first time with Crowley, and Jack starts getting some lessons in humanity. Dean and Cas spend some quality time together, but are...interrupted.

 

Dean knew he should get up. It was almost noon, and even with his excuse to Sam about going to get some, it was still going to be strange for him to be in bed all day. But thoughts of what happened the previous night wouldn’t leave him alone, and he couldn’t decide his opinion on anything. His arm was flopped over his eyes, even though there was no real light in his room, fully dressed in jeans and shirts he wore mere hours ago. 

 

On the one hand, Crowley hadn’t asked him about any of this beforehand. It was a breach of trust, and a huge embarrassment besides. On the other...Crowley had been right. Thoughts like that had been around in his head since he was a teenager, and a life of hunting and one night stands with pretty women had done nothing to silence them. Last night had been everything he dreamt of, and he had,  _ technically _ , consented to it. Most of it anyway. He really wished he could lie to himself and say he hadn’t enjoyed it, but even the thought of it now made his cock start to swell in his pants.

 

“Dean? You up?” Sam’s voice cut through his thoughts and made him pale, his heartbeat picking up as if somehow Sam would just know by looking at him. “Mom picked up some burgers and beer, and I’ve got that hangover smoothie ready, if you need it.” he continued, and Dean’s mouth watered. Less at the smoothie, which he was loathe to admit actually helped with hangovers, since it way too many veggies and not nearly enough ice cream. 

 

“Yeah, I’ll be out in a bit.” Dean said, his voice only shaking a little, which he hoped could be confused with being woken up. He heard Sam walk away, and let out a huge breath, tearing up a little. His family, what was he gonna say if his family found out? What if Crowley was totally full of it, what if he had video or pictures or he was graphic text messages to his  _ mom- _

 

Dean forced himself to stand and turn his lamp on, pacing around the room. There had been more than twenty demons in that bar, and no way to tell who they were. Not really plausible to find and kill them all. He assumed Crowley trusted them, if he let them watch and expected them to keep the secret, but there was no way demons of all things could be expected to keep that under wraps. He stared at his phone, wondering what his options really were. He wasn’t quite ready to call Crowley...he was worried he might say something that would make the demon spill the beans. Or maybe he’d start some phone sex, which was possibly more terrifying. 

 

One thing was certain: He definitely wasn’t going to have sex with Crowley, or any other man, ever again.

 

______________________________________________________________________

  
  


The following week was one of the hardest in Dean Winchester’s very hard life. Acting normal around his family and friends was difficult, since he felt like they could see what he had done in every action he took. Cleaning the car? No more shorts, or music. Business only. Food? Heaven forbid anything but steak, burgers, and beer. The others didn’t notice as intently, but Sam and Cas both were giving him weird looks, but they knew Dean well enough not to press him.

 

Now that things were relatively less apocalyptic, Mary had suggested some kind of schooling for Jack. Maybe even college, if he wanted, but he needed to know the basics first. Bobby would be the main one teaching him about hunting and monster lore, with everyone else helping some. Mary was human culture and blending in, since she’d made a point to retrain herself when she’d been brought back, and as a novice to new tech and fads, she was better equipped to teach a fellow newbie. 

 

Castiel would, of course, be teaching him everything angel related, but also how humanity and angels related to one another. He would also help with history, outside of the books Jack was blazing through one after another. Sam would be handling all the basic school stuff, the brainiac he was, like math, geography, how to research and find information he wanted, and all the boring stuff Dean didn’t have the patience for. Which left Dean with driving and cooking, the two most important life lessons. 

 

After the week from paranoid hell, Dean was finally starting to relax. No one had heard anything from anyone, no sexts from Crowley...he was starting to think things were getting back to normal. It was one of the driving lessons, which Jack was doing wonderfully at, that he started to realize that wouldn’t be the case. 

 

“OK, take this turn slow...thatta boy. You’re getting pretty smooth with those. We’re gonna have to let you pick out a car from the garage if you keep this up. With a little help from me, chicks will be all over you.” Dean said, grinning with his arm out the window, using the other to pat the Nephilum’s shoulder. Jack had picked up on driving like he did everything: really freakin quick. Now it was mainly an excuse to go out for a drive and get out of the bunker, but Dean was thinking about finding somewhere they could practice driving in some life or death situations. Jack didn’t reply for a bit, which was unlike him, and eventually pulled into a gas station. Dean peaked over and saw that Baby could use a refill, but normally he prompted it, not Jack. 

 

“Dean, that’s something I’ve been meaning to ask you about.” Jack said, getting out and pulling out his wallet, half distracted by remembering how to pay for everything, which Dean had only had him do twice. “Why do I want girls ‘all over me’? Shouldn’t I be trying to keep a low profile? I thought the point was  _ not  _ to be noticed.”

 

“Well, a lot of the time, yeah. But hunting can get kinda lonely, so some occasional attention from the ladies helps to relax, blow off steam, ya know.” Dean said, not entirely sure how he felt talking about this with Jack. The kid was looking at him with confusion as they waited for the tank to fill.

 

“But I have you, and Cas, and Sam, Mary and Bobby...why would I get lonely? I know we sometimes go in smaller teams, but I’ll have you guys with me most of the time, right?” Jack asked, and Dean felt his face fall. Surely this was not the first time this had come up, was it? Was he really the unlucky soul?

 

“Jack...has no one...did none of the others, when they were teaching you, say anything about...uh...how humans reproduce?” Dean hedged, his eyes going to the sky in a desperate attempt at receiving heavenly assistance. None came. “They didn’t tell you about sex, at all?”

 

“Well, Castiel mentioned it briefly when he was talking about how humans started out and all, with the Garden of Eden. But he said it would be better to have you or Sam talk to me about it, since he wasn’t sure if it was something I should be learning about yet.” Jack said, that ever curious look on his face holding a ridiculous amount of innocence in it. Dean wanted to say something to argue, but Cas had a point. Given Jack knew how to shoot, kill, drive, and all sorts of other things adults did, sex was probably something he should know about too.

 

“Alright, well...let’s grab something to eat, and I’ll give you the gist.” Dean said, both of them hopping in the car, Dean directing Jack to a nearby diner. He got them a seat in the back, away from everyone else that might overhear the embarrassment that was likely about to take place. He waited until the waitress gave them menus before even broaching the subject. “So...sex.”

 

“Yes. I’ve been curious about it for some time, since I thought it was just how humans made more of themselves, but both you and Bobby have made comments that make it sound...fun? Is it like a game?” Jack asked, looking up with his menu with a frown, the phrasing putting all sorts of jokes in Dean’s head that he had to swallow down. The kid was adorable, and he didn’t need Dean making a bunch of jokes he didn’t understand. 

 

“Not exactly. So, technically, yes, sex is how men and women get together to make babies. But your grandpa has a sense of humor, so he also made it one of the best things we got down here. Which...now that I think about it, was probably to make sure us humans kept having babies.” Dean said, his thoughts interrupted when the waitress came back and he had no idea what to order. He let Jack order, and it sounded alright, so he got the same thing with extra bacon. 

 

“Best thing, like the most fun?” Jack said, looking excited. With that kind of enthusiasm, and the face the kid had, whatever girl landed him was gonna be lucky as hell. Dean forced his thought not to wander in any direction that would cause him guilt later, and nodded with a considering look on his face.

 

“Yeah, it’s fun. It’s...god, I don’t know how to describe it without it sounding gross. It sort of is gross, I guess, but in the best way. Like getting messy because you’re eating something damn good. Which, in some cases...anyway, the guy takes his...you know what.” Dean said, nodding his head down and looking south, which just seemed to confuse Jack further. “...you don’t know what. Your, uh...the thing you pee out of.” he whispered, making sure they weren’t gonna be overheard.

 

“My penis? I thought that was just for going to the bathroom.  _ That  _ has to do with sex?” Jack said, keeping his voice quiet. He was getting better at social cues and keeping things under wraps, which was probably Mary’s influence. Dean nodded and gave Jack a brief, very scientific description of the birds and the bees, how sperm plus egg made baby, and how women were a little different from guys. “I think I get it, but where does the fun part come in? After the baby is born?”

 

“Oh no, for the most part people don’t do it to try and have kids. I mean, some people do, and some people just let it happen if it happens, but for people like us? Hunters? Normally we just do it to have fun, release stress, celebrate the end of a good hunt...that kinda thing. It, uh...feels really, really good. Like, the best thing ever. You know how you feel after having a long shower after a hunt? And then biting into a really nice burger once you’re all clean? Yeah, better than that, by a lot.” Dean said, thinking back to all the great times over the years, clearing his throat and drinking some water when he felt blood rushing south.

 

“Wow...that sounds amazing. Why haven’t you guys told me about it before? I’d love to try it.” Jack said, both men shutting up as their food arrived, Jack frowning and leaning back over as he started to dig in. “Is it because I’m not human? Would it not work the same for me? Is it...dangerous?”

 

“No...well, actually, we may wanna ask Cas about that one. I think it’s the same, mostly, for angels and humans. Reason we didn’t tell you, is you haven’t even been around for three years, Jack. Most humans learn about this kind of thing when they get to be a teenager. You’re still young, and still learning, but...you’ve also had to deal with a lotta crap that most kids don’t. You’re smart, too, and you’re got the body of an adult, so...I figured if you were gonna deal with all the bad stuff, you’d better have the good with it, right?” Dean said with a smile, starting to munch on his bacon. 

 

“So...when can I have sex? And how do I find the right person for it? Do you just ask around until you find someone you’re attracted to?” Jack asked, looking down at his plate for a few seconds in contemplation, some of his hair drooping down. Dean refrained from fixing it, distracting himself with the thought of getting Jack a haircut. “And how do I know if I’m attracted to someone? I know when I like a person’s smile, or the color of their shirt, but how do I know I want to have sex with them?”

 

“Woah there, cowboy. Might be a little early for you to do the deed with someone just yet. We’ll talk about how you go about scoring with the ladies later, but as far as how you know you’re attracted to someone, well...you just kinda know. You get butterflies in your stomach, you smile a lot when you see them, you like it when you’re physically close to them...you light up when you see them.”

 

_ Castiel _ .

 

The thought was quickly removed, suffocated with a pillow, and it’s body dumped in a ditch, before being drenched in gasoline and lit on fire. Dean drove himself far away from that thought at 100mph before being distracted by Jack’s eyes beginning to glow with golden light, the Nephilum using his menu to hide any potential viewers.

 

“Like this? I thought only angels and people related to them could make themselves glow.” Jack questioned, and Dean just stared for a moment. He’d never allowed himself to really appreciate what a gorgeous effect that was, Jack showing the world his power from the inside. Not the white hot light of heaven, nor the sinister light of his father. It was just Jack.

 

“Uh...no, not like that. Sorry, I know you’re still getting used to phrases. Nothing to do with butterflies either. Um...alright, well, since we’re talking about sex, sometimes your dick might get hard when you think about them, or if you’re close to them. Or, you know, they touch or rub up on you or something. Everyone’s different, but especially when you’re young...boners are probably a pretty good indicator.” Dean said, scarfing down some food and trying not to think about some of the erections he’d gotten in the presence of some very not female people. Jack was silent for a moment, processing, which let Dean eat quite a bit.

 

“But, that’s happened mainly around you.” Jack said with confusion, a big bite of eggs frozen halfway to Dean’s mouth as he stared into the younger man’s eyes. “And sometimes Castiel, especially when he’s taught how to fight with an angel blade. But mainly around you, when we’re driving or in the kitchen.”

 

Dean was silent, food still hovering in front of his face while the waitress asked if they enjoyed everything. Jack answered they had, paying for the meal and thanking her while Dean attempted to digest what had just been told to him. The hunter was trying to think of alternate explanations, other reasons this may have happened around him for Jack. I mean, sometimes guys got them when an exciting situation was going on, right? But this was apparently  _ only  _ happening around him and Cas. 

 

“Not, uh...not around Bobby? When he’s teaching you how to shoot? Or, heaven forbid, mom?” Dean asked, and Jack just shook his head. Dean put his food down, a weird feeling in his stomach that felt like a fusion of excitement and guilt. “Well, it might not mean that you’re...you know. I’ll try to ask Cas sometime in the next couple days, maybe it’s a weird angel thing.” he continued, thankful as hell that Jack just nodded and finished his food. 

 

“I’m excited about trying it, but I get if you guys think it’s not a good idea for a while. Are we going to head back?” Jack asked, Dean just nodding and getting up, ignoring their waitress and walking out the door, a hurried thank you shouted from Jack as Dean hurriedly got in Baby. He gave a big sigh of relief when the engine was rumbling, taking a couple deep breaths before Jack got in the car. There was another explanation, right? No big deal.

 

_____________________________________________________________________________

  
  
  


Dean wanted to ask Cas about what he found out, he really did, but when the angel asked if he wanted to watch a movie together...he didn’t want to ruin their time together with a serious talk. It had been so long since they’d been able to relax and not worry about the world crashing over their heads. Sam and Bobby were combining their efforts to organize hunters around the country, giving them info from the bunker and helping get teams together that could take care of jobs easier and faster than before. Charlie was even helping, getting back into the tech arena by going on forums and other sites to connect new hunters to their group. With all their hard work, their family hadn’t had to go out on a job for weeks.

 

Cas had let Dean pick the movie, which made Dean feel warmer inside than he liked, since he knew a lot of what Cas did was to humor him and learn about human culture. Dean picked an old western favorite of his, telling Cas personal stories about when he had watched it when he was a kid, what had been going on...just sharing. Cas’s eyes were on him more than the television screen, smiling, and Dean found it harder and harder to care about the movie. At least, until his phone buzzed, and he looked at the screen.

 

_ You have two minutes before I call, and you should probably be out of hearing distance _ .

 

From Crowley. Dean excused himself, stuttering slightly, and could feel Castiel’s frown from behind him even as he told him to keep watching the movie. He didn’t exactly run to his room, but it wasn’t walking. He paced as he waited for the phone to ring, jumping when it buzzed in his hand. He gave it two rings before he swiped and brought it to his ear, not saying a word.

 

“Dean. It’s been one week, almost to the hour, since we last spoke...how are you?” Crowley asked, and Dean’s mouth opened but no sound came out. Crowley’s voice sounded just as it always did, but now he knew what kind of things that voice could say in the heat of things, and it changed how he thought about it. He looked at the door to his room, walking over and locking it before whispering. 

 

“What do you want, Crowley? I’m busy.” Dean said, trying to put annoyance in his voice while still keeping it down. The demon chuckled on the other end of the phone, and Dean closed his eyes when he remembered the last time he heard that. Memories were trying to flood back into his head, but he pushed them back.

 

“Now, is that any way to speak to the man of your dreams? I say that, since I’m sure you’ve dreamt about me since the Big Event.” Crowley said confidently, Dean frustrated to admit to himself that Crowley wasn’t wrong. “I’m just calling to make sure you’ve had enough time to recover, work your head around a few things, and if you’d be interested in a repeat performance? Tonight, ideally.” Dean felt like his blood was freezing in his veins, even as a sweat broke out on his forehead. He hadn’t expected to be  _ asked _ , like Crowley was asking if he wanted to go catch a movie. 

 

“Why the hell do you think I’d ever want to see your smug face again, asshole?” Dean said, calling on all his years of bullshitting to cover up the fact that he felt like he was sixteen again, his stomach doing flips and his dick trying to bust out of his pants. Crowley asking him was getting him hard for god’s sake, he felt like his whole body was betraying him. 

 

“Do you not remember what you said last time you saw my smug face? ‘Yes, Crowley, please cum inside me, I need it.’” Crowley said, his voice briefly turning into an exact duplicate of Dean’s, making his face pale and eyes squeeze shut as he remembered the feeling of Crowley plowing into him, filling him up from the inside, making him bust all over himself. “Quite a hard thing to forget, if you ask me. I know I’ve certainly been thinking about it myself.”

 

“That is  _ not  _ what I said, bastard.”

 

“No? What did you say, then? Refresh my memory.” Crowley asked, and Dean found himself at a loss. He knew roughly what he said. He knew he had begged. He knew he wanted it again, and so did Crowley. “How soon can you sneak out of the house? I’ve got a room within a few miles of you.”

 

Dean could hear his own heartbeat in his ears, every nerve ending he had tingling like it was being licked by flames. Cas was waiting in the other room for him to finish watching a movie. Dean’s dick was hard as steel and aching to go get some of whatever Crowley was offering. But he and Cas were having such a nice, normal time for once, and Cas had asked  _ him _ . He looked over at the clock, it was only about nine. The movie had another hour left, max. 

 

“Dean. If you’re worried about some of what happened last time, you shouldn’t be.” Crowley suddenly offered. Dean slowly sat on his bed, his hand dragging down his face at the stress of all this. He hated how much he wanted this, but his blood was boiling just thinking of doing anything with the demon again. “Last time was a punishment for making me wait. This time will be a reward for coming of your own volition.”

 

“What do you mean?” Dean asked hesitantly. What Crowley had done with him last time was a lot to handle, and embarrassing, but the worst part was how much he had enjoyed it. What did Crowley have in mind for a reward?

 

“I mean, last time was to put you in your place. Now that you can’t deny your appreciation of certain pleasures, I’m going to ensure you enjoy tonight on many different levels. No other demons to be embarrassed by, no restraints unless requested. Just you, me, and some fantastic sex.” Crowley said, and Dean shut his eyes and tried not to picture himself spread out on a bed for the demon, or maybe on top of a desk, and failed. He wanted that one on one time with the demon, Chuck help him.

 

“...eleven.” Dean finally grumbled out, not believing he was agreeing to this. That would give him enough time to finish the movie with Cas, shower, drive to wherever this place was...and maybe have enough room for a panic attack on the way there. He could practically hear Crowley grinning like the cat who got the cream on the other end of the phone. 

 

“I’ll text you the address. See you soon, Squirrel.” Crowley said, the phone going silent a moment later. Dean just held it in his hands, looking down at it guiltily. It buzzed soon after with a text, and mapping out the address, it would only take him fifteen minutes to get there. It took him another ten minutes of staring at his door and making his erection go down before he finally forced himself up and back towards his amazing TV and game room, unable to appreciate how great it was in his current mental state. Castiel was staring up at him as he came in, concern on his face. The angel had removed his coat, the garment folded carefully over the back of the chair, and Dean had to force himself to keep his eyes up his friend’s face. 

 

“Is everything alright? You were gone a while.” Castiel asked, and a small part of Dean wanted to open up to Cas about everything, start spilling the beans. But he was worried about what else would come out if he started talking, that he wouldn’t be able to stop and the angel would never look at him the same. 

 

“Yeah, everything’s good. Sorry for the wait. What part you get to?” Dean asked, his eyes slipping back to the screen as he sat, knowing his face was red and trying not to look too guilty. Cas didn’t answer, and Dean knew he wasn’t fooling his friend, but thankfully the angel didn’t ask. The rest of the movie passed mostly in silence, Dean too distracted by the slow passage of time to make commentary as he had before, but towards the end Cas finally got him talking again a bit, prodding him with small questions that put him more at ease. At least till the credits started rolling. 

 

“Would it be inappropriate for me to ask who was on the phone?” Cas asked, making Dean’s slightly relaxed feelings vanish right quick. He could feel the slightest of accusations in Cas’s tone, making Dean wonder if he had overheard anything. He was an angel, after all. “I don’t want to pry, you just seemed...out of sorts, for the rest of the movie.”

 

“Yeah, no, just something personal. No big deal.” Dean bluffed, knowing the second he looked over and shrugged at Cas that his words weren’t believed. This was the problem with getting close to people. No matter how many police officers and morgue employees you fooled, the people closest to you started to be able to read you. “Really, Cas, nothing important. We don’t have another apocalypse over our heads.” 

 

“I thought...well, I thought we could talk about personal things, now that things are a little quieter.” Castiel tried, and Dean felt himself ache inside at the hopefulness inside Cas’s voice, but couldn’t find the words to reply, looking over at the screen as the credits kept rolling. There was silence for a moment, the urge to tell Cas warring with the guilt and shame Dean felt. He shut his eyes when the angel got up. “I apologize, I know talking isn’t something you enjoy doing often.”

 

He was starting out of the room when Dean snatched his hand, stopping him midstep. Dean tried to enjoy the brief contact of their hands together, but let go after a few seconds of loaded silence. Why did Cas’s eyes have to be so blue? Why did he have to look at him that way, like he was trying to unravel Dean from the inside out? He knew it was just because he wasn’t human, societal norms still something Cas had never gotten accustomed to, but the attention made Dean uncomfortable in ways he didn’t want to put a voice to. He grabbed the angel’s coat from where he’d left it on the chair, handing it to him.

 

“Don’t wanna forget this.” Dean tried with the most awkward smile his face had ever produced. It fell as soon as Cas put on his coat wordlessly, looking at the floor as he did so. “Look, Cas, I  _ do  _ want to talk to you about stuff. I...I know I’m not the easiest guy to have a heart to heart with, but you’re my best friend. This isn’t something dangerous, or world shattering, it’s just...personal. Not something I’m ready to talk about yet.”

 

Cas stared at him for a moment, his eyes looking over the hunter’s face, before giving a small nod. He smiled softly, a bit sorrowfully, before he walked out of the room, and Dean just stared at the angel’s back as he left, screaming every curse word he knew (and there were many) inside his head. He wanted to chase after Cas, but he didn’t know what he wanted to say or do, he just wanted to make him feel better. His phone buzzed in his pocket as he stood there, and Dean numbly took it out and looked down at the text. A picture and message from Crowley.

 

_ Don’t keep me waiting, Squirrel. _

 

For a moment, Dean wasn’t sure what Crowley had sent him a picture of till he turned up the brightness on his phone. It was the front of Crowley’s black pants, and the huge bulge that looked barely contained. It sent blood rushing to Dean’s face and cock, and he closed his eyes, trying to control himself, before he quickly started walking to the bathroom. He couldn’t risk anyone else seeing him in the state he was in, and he breathed out a held breath when the door was finally locked behind him. 

 

Dean Winchester was a very visually motivated and virile man. He had looked at porn, both in magazines and on the computer, more than most men could even fathom, using it as a huge stress relief from the pressures of his life of hunting. His sex drive was pretty damn high, even if he’d been too distracted by the last few world ending threats to get much action. But one thing he had tried his best to refrain from was looking at guys in porn, mostly looking at women on Busty Asian Beauties. Now he had a picture of Crowley’s huge bulge, one that he knew was anything but an exaggeration, and couldn’t stop thinking about how great it had been inside him. 

 

“Son of a bitch...” Dean whispered to himself as he squeezed himself through his jeans, his mouth dropping open at the stimulation. It had been so long since he’d gotten off, he didn’t normally let it go this long, but he knew that if he jerked it he would have thought of Crowley, no doubt. He gave it two minutes of trying to talk himself out of it, then he whipped off his shirt and started on his jeans, walking over and starting the shower up. Maybe he’d have better luck another night, but tonight he needed to see Crowley. 

 

Dean stared at himself in the mirror as the water heated up. He pulled down his underwear and felt himself shiver. He was flush with arousal, his whole chest and back bright red. He was hard as steel, starting to form pre at the tip of his impressive cock. He knew he didn’t hold a candle to Crowley, but he knew he was damn hung, and lots of women’s screaming and sopping wet holes confirmed that for him over the years. He looked...good, maybe a little soft around the middle, but strong looking arms and back. He shouldn’t feel self conscious, but he did. Should he shave? Maybe wear some cologne? He forced himself into the shower before he thought too much about it.

 

He quickly went through his usual quick washing routine, but slowed when he got down south, realizing something. Should he clean himself extra well back there? Should he...his fingers gently brushed his hole before he could stop himself, and he groaned. He turned the water up hotter when he started shaking, standing under the stream and breathing hard despite the lack of effort. That felt way better than he thought it would. He had stopped himself from doing anything like this for so long...but he didn’t have that long before he was supposed to meet Crowley. Later, he promised himself. Now that he was actually doing this, he might as well enjoy the perks when he was going at it alone, right? He just gave himself an extra good scrubbing everywhere, spent one more minute destressing under the water, then shut off the shower and toweled himself dry. 

 

Taking a shower whenever he wanted wasn’t a crime, but he still felt like a criminal as he went back to his room, his dick half hard with thoughts on what was going to happen. It was 10:30, and he forced himself not to stress about what he wore. He wasn’t going to have it on for long, right? Black tshirt, plaid overshirt, and jeans. If Crowley wanted him fancy, he should have said something. 

 

He could feel his breathing coming ragged, and he forced himself to take another minute to calm down, before grabbing his wallet and other essentials. He was thankful for most souls being early risers in this house, no one stopped him as he walked down the halls and towards the garage. He knew Cas would be awake...god he felt guilty about how he’d acted around him, but he promised himself he would make it up to him. Just as soon as he dealt with his...personal matter. 

 

Baby helped calm him almost immediately, the engine’s purr easing his breathing and racing heartbeat as he mapped out where he was going, the picture of Crowley’s bulge just below the address he needed. Fifteen minutes away. 

 

He would make it in ten.

**Notes for the Chapter:**

> Gonna be a hot one next chapter, folks. Bring some water and a fan.


	5. Motel Renovations

**Summary for the Chapter:**

> Dean takes Crowley up on his offer for a motel meetup.

**Notes for the Chapter:**

> Sorry this took so long! Life is crazy right now, trying my best to update on a regular enough basis.

 

Dean pushed the limits of what was both safe and legal as he sped along towards the motel Crowley had texted him about. He was terrified, since he had no idea what exactly was waiting for him, or what Crowley had meant by ‘reward’...and also incredibly excited. His legs were constantly shifting, trying to ease the pressure in his pants that wouldn’t quit. He begged whatever deity was listening not to have their be any cops watching, he really didn’t want to be pulled over. 

 

He only slowed down when he came to that final light. He could see the lights for the motel in front of him, and he stayed at the light when it turned green, then red again, then green...and finally forced himself to drive that extra little bit into the parking lot. It was like most other places him and Sam had stayed at, other than having some construction work done in some areas. Dean only then realized that Crowley hadn’t told him a room number, and texted the demon with shaking hands.

 

_ here, which room? _

 

He found himself trying to convince himself to leave, which promptly failed when the demon replied.

 

_ First floor, room 66. And please Squirrel, relax, stop shaking. I’ll only bite if you ask. _

 

Dean started, looking out Baby’s windows and trying to see where Crowley might be watching from, but couldn’t see anything helpful. Maybe he just guessed? Either way, he leaned his head back against the headrest and closed his eyes, taking a few deep breaths before getting out of his car. He looked back at the trunk consideringly, but he was already making one bad decision, why not another one? If Crowley was trying to screw him over, he knew he couldn’t take on the armies of Hell with an angel blade and a shotgun. Crowley was smarter than that.

 

He walked around a little, feeling exposed like the idiot he was being, before finding the most central room on the first floor, which definitely shouldn’t have been labeled 66. For starters, the closest room to it was numbered 24, and the door was bright red, where all the others were beige. He just stared at the number for a solid two minutes before he turned the knob, taking one more deep breath before he wanted into...what was most definitely not your average motel room.

 

For one thing, hotel rooms did not have vaulted ceilings. Most were not professionally painted in blacks and silvers to this degree...nor did they have carpets this nice, crown molding of any kind, or expensive artwork adorning the walls. Or a huge fireplace, with two huge armchairs turned towards it. Or a beyond king sized bed with lush, burgundy fabric draped from its posts. Or the room to hold all of this in. What the hell?

 

“It’s about time, Dean. I was worried you’d had second thoughts at the door.” Crowley said, walking over from the hunter’s side and making him jump. The demon was in a black, silk robe, and held two glasses in his hand with amber liquid inside them, offering one to Dean. The hunter took the glass, not drinking yet, and motioned around at everything with it. 

 

“Crowley...what the hell is all this? Did I walk through a portal, or is this all really...real?” Dean asked, wondering how this could have possibly been done without anyone noticing. Other than a door leading to what was likely a bathroom, there were none of the other doors he saw outside anywhere, just the one entrance.

 

“Well, after our fun little tryst, I decided I couldn’t just invite you to random locale any time we wanted a  rendezvous . So I decided to find a nice spot nearby, someplace no one would notice, and fix it up a little. A few rooms will be kept the way they originally were, of course, but only for emergencies. Once the spells and wards are in place, and a little technological adjustments, no one will know this place is here. Besides you, myself, and a few select demons, of course.” Crowley explained, putting a hand on Dean’s shoulder and leading him to sit by the fire.

 

“This...you made this for  _ me _ ? For us to...you know. Seriously?” Dean asked, looking around incredulously. He didn’t want to think about how much this cost. “Wait, you started this a week ago? How the heck is so much of it done?”

 

“Well, Squirrel, you and your motley crew have inspired me to change Hell up a bit. So, I thought, why put all those great artists and builders down below to waste? Why not offer them a reprieve from torture in exchange for their skills? Those who show good work might even get positions elsewhere...productivity is the name of the game now, and it’s all thanks to you.” Crowley said, cheering Dean with his drink before taking a slow swallow.

 

“Thanks, I guess...” Dean said looking down at his glass and swirling the drink around for a minute before taking a small sip. If Crowley wanted to drug him, he could probably just have a team of demons grab him again. It was almost a comforting thought, things being out of his hands. “This is good stuff.”

 

“Always. Now, onto more important matters. The matter of your reward.” Crowley said, and Dean couldn’t make himself raise his eyes, just staring into his glass. He could feel his heart rate increasing, his face heating up, and the initial shock of the impressive room going away as he felt Crowley’s eyes on him. His eyes moved up at the demon’s next question, however. “What would you like to do, Dean?”

 

“What do you mean? Aren’t you...you said no restraints, but I thought...” Dean let his question wander off, realizing he’d still been under the assumption that Crowley was going to take charge, even with his talk indicating otherwise. 

 

“Come now, Dean.  _ Clearly  _ you hated being tied up and forced to do things my way. So, as your reward, I’m letting you run the show tonight. You’ve never done things with a man before me, correct?” Crowley asked with a smile, Dean only hesitating for a second before nodding. “Well, now’s your chance to explore, to try things you haven’t before. What have you always wanted to try with another man?”

 

Dean’s thoughts raced to places he didn’t often let them roam. He knew he’d always wanted to do stuff with men, but he’d purposefully not let himself get too far into detail. He thought of what Crowley had done to him last time, and how amazing that had been, how much he wanted more. But he didn’t want to admit to Crowley just how well he’d hit the nail on the head, how he wanted nothing more than to be bent over on that huge, expensive looking bed until he and Crowley broke it through their efforts. 

 

“...I don’t know.” he finally settled with, Crowley letting out a disbelieving laugh which made Dean’s face turn even redder. His cock was starting to harden with the thoughts in his head and Crowley in nothing but a robe. “I  _ don’t _ , asshole. I didn’t give it much thought. I like girls, doing girls, and thinking about doing girls.”

 

“Oh, I know you do. Let me make one thing clear, Dean. In no way do I doubt your appreciation of women, nor the dozens and dozens of the fairer sex you’ve left satisfied across the country.” Crowley said, putting down his drink and stepping closer to where Dean sat, putting a hand on his shoulder again and leaning down to look him in the eye. “It’s just that I think you want men even more, and you’ve let yourself go an unfortunate amount of time without enjoying the sins of the flesh with other strapping lads like you.”

 

Dean’s lips parted slightly as Crowley’s touch and words forced his cock to full attention, his eyes on the demon’s mouth, wishing one of them would just close the distance already. Instead, the demon’s hand slid down the length of Dean’s body, forcing a breath out of him when it settled on his stomach, just above the huge bulge in his jeans. Crowley kept it there, locking eyes with him. His drink fell out of his hand, forgotten. 

 

“Now, what do you want me to do right now, Dean? What would be a suitable reward for being such a good boy for me last time?” Crowley said, almost whispering. Dean’s hands were gripping the supple arms of the chair like it was his last lifeline, feeling a wet spot start to form in his pants. He remembered how easily he’d been forced to cum last time, and how good it felt. He wasn’t sure he’d be able to last any longer this time, especially after a week of nothing.

 

“Kiss me? Please? And please,  _ please  _ don’t tell anyone about this.” Dean begged, breathing raggedly as Crowley came a little closer and grinned. He could feel the heat from the other man’s body, and groaned in agony when the demon removed his hand and stepped back. Crowley’s huge cock was covered by the thinnest fabric Dean had ever seen, the outline of the head clearly visible. It would take so little to reveal it in its full glory. 

 

“No one will hear it from me, or my demons. I’ve been trying to get them to tell others in Hell, but they just can’t manage it for some reason.” Crowley said with a sly grin. Dean just looked at him, confused and desperate. “I’ll tell you later. Do you want clothes on or off? Because once I start kissing you it might be a little hard to get anything as complex as undressing done.”

 

“Off, definitely off.” Dean said, standing and feeling like his blood was going to boil out of him. Crowley looked at his bulge and hummed his appreciation, Dean realizing he was actually going to have to strip for the demon. Their eyes met again, and the sure smile Crowley gave him was enough for him to start stripping off his shirts.

 

“You look good enough to eat. Play your cards right, and we’ll both find out if that’s true.” Crowley suggested, Dean just grunting while he kicked off his shoes and worked on his pants. The king of hell just slowly untied his robe, sliding the smooth fabric off his shoulders and revealing his mammoth member to the eager hunter. “If you’re going to take this long, I can always come back later.”

 

“Shut up, just shut up.” Dean ordered as he finally got his underwear off, his eight incher swinging and probably dripping on the carpet as he closed the distance between them, their mouths connecting like lightning strikes a skyscraper as they attempted to devour one another. Kissing Crowley was different than any woman he had been with; his tongue was thick and seemed to fill his mouth, and he did things with it no one night bar hookup had ever done. 

 

Dean groaned loudly into the demon’s mouth as their cocks slid together, his voice cracking and going higher when Crowley took a firm hold of his ass with both hands and yanked Dean higher and closer. Feeling a thrill go through him at the demon’s strength, Dean wrapped his arms around Crowley’s neck as he walked them to the bed. The hunter shook as he was essentially tongue fucked and lowered down to the bed, Crowley’s hands starting to explore as Dean just tried to hang on for the ride, broken noises escaping from his lips whenever Crowley let them. It only took a few minutes of the demon grinding on top of him before Dean felt himself getting close to cumming, but Crowley lifted himself off of him and grinned down, panting.

 

“Not so fast, I won’t have you surprising me again with your lack of self control.” Crowley muttered, leaning down and stealing one more kiss before rolling himself off Dean, opening the drawer to the end table by the bed and rummaging around inside. Dean just looked up at the ceiling and breathed raggedly, painfully hard and trying to convince himself this wasn’t the hottest make out session he’d had since...ever. “Now, think you’re up for wearing this? As with everything tonight, I leave it up to you, but this will be a lot more fun if I don’t have to worry about you going off like a shot.”

 

Dean looked over and cursed inwardly at how surprisingly hot Crowley looked in the firelight, he had thought the guy just looked good in a suit. He peeked down at the large ring in the demon’s hand, his brows coming together. It looked like a cock ring, but one that was way too big for him, or any man. He’d only worn one a couple of times in his life, but he was pretty sure they needed to be a little snug. Looking closer, he was pretty sure he saw some writing on it.

 

“I’m flattered, but I always told Sam I’d marry for money. That’s not gonna fit on my dick, Crowley, I’m not  _ that  _ big. You’re not even that big.” Dean protested, Crowley smirking and placing it around his own shaft and balls, almost having a hard time getting it around both. Dean hadn’t been able to notice as easily before, but Crowley had huge balls too. They looked...full.

 

“It’s enchanted. Observe.” Crowley said, snapping his fingers. The ring tightened snugly around his member and balls, and the demon let out a pleased little grunt. He stroked himself a bit, Dean’s eyes unable to look away. “More entertaining options than this too, but for tonight I thought it would keep this all from finishing too quickly. But tonight is about you, and your desires, so if you think you can control yourself...”

 

“Gimme the damn ring.” Dean muttered, Crowley snapping again and transferring it over to Dean, the hunter letting out a small moan when Crowley’s fingers moved and played with his sensitive balls to get it on. He tried and failed to stifle a gasp when the demon snapped again and it tightened around him, making him impossibly harder and wild with the realization that he might not be allowed to cum without Crowley’s permission. That should not turn him on as much as it did, he thought with embarrassment. 

 

“That is a splendid sight...what I wouldn’t give for a professional photographer at the foot of the bed. Now, Dean, where were we?” Crowley asked innocently, and Dean practically launched himself on top of the demon, picking up where they left off, rutting and feeling one another as their tongues played together. Dean heard himself actually whine when Crowley grabbed both his ass cheeks firmly and started to use his body to stroke his massive cock. “You  _ like  _ that, don’t you? Like being used? No wonder you couldn’t get enough last time.”

 

“Do you  _ ever  _ stop talking? Fuck, you’re strong.” Dean complained/complimented as he was used like a rag doll, his cock getting almost as much stimulation as Crowley’s. He felt light headed, like he was floating, constantly struggling to stay focused on what he was doing instead of just letting himself be a living sex toy. “I...oh shit, I thought I was in charge.” he said roughly. Crowley stopped his grabbing, settling his hands gently on Dean’s hips as the demon smiled up at him.

 

“You’re quite right. What would his Majesty wish for his humble servant to do for him?” Crowley said with mock servitude, raising an eyebrow, and Dean was thankful for the snark. He took some deep breaths, focusing his mind and rising to the challenge, lifting himself off the demon and scooting up his body, his impressive manhood jutting out a few inches from Crowley’s lips. Their eyes didn’t break from staring at one another.

 

“Suck my cock, bitch.” Dean said with as much authority as he could muster. For a moment, the smile on the other man’s face made Dean nervous he was about to get bitten, but then some of the softest lips he’d ever felt started working their way over the head of his dick. Crowley started slow, with teasing touches and gentle licks, and Dean felt his stomach muscles flex without his say so the longer the agonizing treatment went on. “Come on, Crowley, I said suck.”

 

The speed and ferocity with which the demon started sucking on his cock nearly made him scream. Dean let out a strangled cry as he caught himself with his arms, keeping himself suspended in a push up position. He was staring down as Crowley sucked harshly and almost painfully on his most sensitive area, causing gasps and curses to leave his mouth without his permission. 

 

“Easy, Crowley, a little easier.” Dean finally complained, and the demon surprised him by popping Dean out of his mouth and manhandling him, flipping them over so Dean was on his back with Crowley between his legs. “Watch it, I’m not a sex doll, dude. Ooooh, god...” he managed as Crowley engulfed him again, this time doing something totally different with his mouth that Dean was almost sure had to be illegal. 

 

“Better?” Crowley said, using his hand to stroke Dean slowly up and down. Dean couldn’t even nod, just arch up and moan as Crowley deepthroated him, his mouth soft and silky and not aggressive at all anymore. Several minutes of that treatment had Dean’s legs shaking and voice quivering; this was the best blowjob he’d ever had in his life, and that was saying something. The only thing that was keeping him from firing off a huge load was that ring around him. “You can participate a bit, you know. I’m not like those blonde bimbos you pick up in bars, I’ve been to hell.”

 

It took Dean a solid minute of half-coherent thought before he realized that Crowley wanted him to fuck his mouth. He slowly moved his hips, letting himself get in sync with the demon sliding down his shaft, and swore loudly at the extra pressure he got at the back of Crowley’s throat. He got into more of a sitting position and brought up a hand to grip the back of the demon’s head, starting to actively shove his friend’s mouth down on his cock, the slick noise of a messy blowjob just heightening both their arousal. 

 

“Oh  _ fuck  _ yes, Crowley, that feels so good. You’re so fucking good at this, take that big cock right down that throat.” Dean ordered breathlessly, loving the fact that the rougher he got, the more Crowley seemed to enjoy it. He never got to be this rough with women, but the demon clearly didn’t mind. His eyes never left Dean’s, despite the hunter sometimes needing to shut his eyes or look skyward and moan. Dean’s breaking point came when Crowley started teasing his hole with a finger. “I need to cum, I need to cum now Crowley,  _ please _ .”

 

He hadn’t expected it to be that easy, but with the sound of a snap the ring loosened itself around him, and his eyes bugged out as his orgasm rushed up to meet him like a freight train. He thrust himself upwards and pushed down on Crowley’s head with all his might, the demon making a beautiful strangled sound as he was impaled on an erupting volcano that was pouring a weeks worth of cum into his gullet. Dean couldn’t form words, just howling as the spunk was emptied from him, Crowley’s tongue constantly moving even though his head wasn’t allowed to rise. 

 

After one of the longest orgasms of his life, Dean collapsed backwards onto the bed and let go of Crowley, covered in sweat and unable to do anything but attempt to gulp down air and let the tears fall down the sides of his face. He had never considered himself a religious man, even given all he had seen, but that had been a religious experience. 

 

“You know, that somewhat defeated the purpose of the ring...though I can’t say the results were unpleasant.” Crowley said, cleaning his mouth up as best he could after swallowing so much cum. He slid up to Dean, lying on his side and watching the man try to get his breathing under control, gently moving his fingers up and down his chest and stomach. “Remind me to do that to you more often, you’re quite something when you’re verbal.”

 

“I’m...not...” Dean started, but needed to take a few more deep breaths to even consider continuing, his heart finally starting to calm itself. His whole body began to feel sated and relaxed, and he wiped a little of the sweat off his brow. “I’m not usually that verbal. With...girls. Not unless I know they like it. That was...geez, Crowley, I’ve never felt like that. And I’ve had a fair share of blowjobs.”

 

Before Crowley could respond, Dean surprised himself by turning onto his side to face the demon, hesitantly putting his hand on his side. The demon smiled and got closer as well, encouraging him with a hand stroking his arm, letting Dean feel comfortable enough to close the remaining distance between them and start kissing Crowley. It was different than before, a little less desperate, Dean trying to thank his friend without words. The message was received loud and clear, especially when Dean moved his lips to the demon’s neck. 

 

“Well, I’ll take that as a sign of a job well done. Don’t get me wrong, Squirrel, I love the idea of making you my bitch any day of the week, but I can take it as well as I can give it. I’m welcome to exploring our options.” Crowley said, letting out a pleased him as Dean lowered himself further, his fingers exploring the demon’s chest but ceasing his kissing. “What’s wrong?”

 

“Just...never had a chest with hair on it. Not like this anyway.” Dean said, almost to himself. Crowley could see the emotions warring inside him. Guilt, fear, wonder, lust...the demon wanted to roll his eyes, but restrained himself. He literally ruled Hell, but Dean seemed to be full of more guilt and regret than most of the swine down in the pit. He put his fingers under Dean’s chin, lifting it up to look at him in the eyes. 

 

“There is absolutely nothing wrong with liking both men and women, Dean. And I would know if anyone got sent to hell for taking it up the rear. So far, the count is zero.” Crowley assured him, Dean dropping his eyes and playing absentmindedly with the demon’s chest hair. He seemed to be in thought, and Crowley satisfied himself with running his eyes over the naked, sweaty hunter.

 

“It’s not that I think that anyone liking the same sex is wrong, I know it’s not. I’ve got no problem with Charlie, or anyone else liking whoever they want. Sam could tell me he liked getting it on with Wendigos, and I’d find a way to deal. It’s just...me. I shouldn’t. It’s not how I was raised, it’s not how I lived my life-”

 

“You’ve literally saved the planet, you insufferable, repressed idiot. I’ve dealt with quite a lot of men who possess issues with their sexuality, and for most of them I can understand it. But you’ve killed the Devil, met God, and made out with his sister. Try to have a little perspective. Suck a dick, or eat a pussy, you’re going to be the savior of mankind either way.” Crowley said, Dean staring up at him for a solid minute of silence. Before he sunk down to where the king of hell’s dick rested against his thigh, lifting it with his hand and starting to suck on the thick head. 

 

“There now, that’s a much better use for those beautiful lips.” Crowley said, giving a few pleased sounds as Dean suckled him back to hardness, the hunter taking his time and exploring around Crowley. Occasionally Dean looked up to check if whatever he was doing was alright, with nothing but positive signs from the demon. Crowley grinned when Dean took in a bit too much and choked on the massive rod. “Careful, no demonic mojo to help you this time.”

 

“You’re too fucking  _ big _ , Crowley. I don’t know how I’m still alive after this thing.” Dean halfheartedly complained, his wide eyes not leaving the huge pole as he stroked it, his hand barely able to fit around the thing. Already he was breathless, hard and interested just from playing with it. He wanted to try to do more, fit more, but it actually scared him how eager he was to take this thing. 

 

“A change of position might help. If you climb up top, might be easier...I can’t promise I’ll keep my tongue to myself though.” Crowley said, running his hand through Dean’s hair and noting with satisfaction how the green eyes closed in contentment, before the hunter nodded and climbed on top of Crowley. There was a little scuffle when the demon forced Dean’s legs apart on either side of his chest and gripped and massaged his legs, Dean nervous to expose himself so readily to the other man without a token sign of resistance. 

 

“Easy back there, I’m not...I don’t-” Dean started, his mouth falling open as he shut up. Crowley had spread his cheeks very wide, and was clearly examining his hole. His thumbs brushed some of his most sensitive areas and Dean had to force himself not to make any noise, collecting himself as best he could even as his cock throbbed against Crowley’s chest. “I did my best to clean up back there, but I don’t know if it’s...enough.”

 

“I’m a demon, Dean. I don’t really care one way or another. But if it bothers you...” Crowley started, snapping his fingers and sending a powerful  _ zing  _ through the hunter’s lower half. The demon leaned forward and started lapping at Dean’s hole, which surprised the man into moaning much louder than intended. “There, clean as can be. And far too tight for my liking, I’ll need to fix that.”

 

With that, Crowley dove in, using his thick tongue to lazily lap and poke at Dean’s hole, the other man cursing and resting his head by Crowley’s cock as sensations he’d always dreamt of but never experienced washed over him. He wanted to return the favor, but he could only lie there for a few moments, basking in the attention the demon was giving him. It felt so good, almost better than a blowjob, and he couldn’t stop the whine that came out of him when Crowley started to feel the slick hole with his fingers. 

 

“Now, I’m all for focusing my attention on your hole, for the entire night in fact...but you’re still in charge of tonight. So long as you want to be. And since this seems to be distracting you just a bit, well...do you want me to keep going?” Crowley said, thrusting his cock up a little to emphasize what Dean had been neglecting. The hunter wracked his brain for an excuse he could use to keep Crowley playing with his ass without admitting outright that he was loving it. 

 

“Sorry, I’ll stay focused. And you...you don’t have to stop, if you don’t want to, back there.” Dean said, his face flushing. He started stroking the huge cock he held, having to get up a little higher to even get it in his mouth, but he hummed in satisfaction once he got a taste of Crowley’s precum on his tongue again. He sank down a few inches, thrilled that this position let the demon’s monster cock slide down easier, letting him get more in without choking. 

 

_ Not that the choking is really a  _ bad  _ thing _ . Dean thought to himself, groaning when Crowley started to gently press a finger into his ass. His cock was starting to leak; he could feel it slowly dripping, which wasn’t normal for him so soon after cumming. He forced the fifth inch of dick down his gullet, his mouth filling with saliva and precum when he heard Crowley’s pleased moan.

 

“For a novice, you’re really quite good at that, Dean. I’d like to cum in your mouth, and for you to swallow, if you think you can manage it. But not till you get at least half of it down your throat.” Crowley said, summoning a bottle of lube from the bedside table with a flick of his fingers. Dean hummed what the demon was quite certain was agreement, but took himself off the cock in his throat when Crowley slipped a lubed finger all the way inside his ass in one go. 

 

“Christ, Crowley! Oh god, that feels...fuck...” Dean protested, pleasure burning its way through him alongside the small amount of pain. Tears were coming to his eyes; he couldn’t believe he was letting the demon inside his ass again, and that it felt so fucking incredible. It was like he was having a fire started inside him, just like last time. Crowley gently started thrusting his finger in and out, making his gasp and grip the cock in his hand tighter. “Jeez, why does that feel so damn good? It’s like you’re stroking my cock from the inside.”

 

“Do you mean to tell me that, with all the monster lore and spell incantations in that lovely head of yours, you don’t have a concept of basic male biology? There are plenty of pleasurable spots for me to stroke inside this tight little fuckhole, including, of course, your prostate.” Crowley explained, using on hand to spread Dean’s hole farther and get his finger as deep as it could go, wiggling it around and making the hunter cry out as he was stimulated from the inside.

 

“I skipped a  _ lot  _ of school, Crowley. Jesus,  _ please  _ go easy, you’re driving me crazy.” Dean begged, relaxing for a few seconds when Crowley withdrew to add more lube. That ended when the demon forced two fingers inside him slowly, making Dean grit his teeth before he slowly blew out all his breath as pain and pleasure made sparks dance in front of his eyes. “That is  _ not  _ what I meant by easy, asshole! Fuck!” 

 

“Please, compared to all the broken bones and bites, what’s a couple of fingers between friends? There we go, just let me in.” Crowley said calmly, watching his fingers sink in the rest of the way, stretching the hunter’s beautiful hole and making the cock nestled against his chest leak even more. “Distract yourself with my cock, you need to get as much as you can inside that throat. And tell me if you want a little help from me to force it down.”

 

Dean hurriedly started sucking on Crowley’s big cock, trying to stop himself from making more embarrassing noises when the fingers inside him started moving gently. He wanted Crowley to face fuck him again,  _ badly _ , but he needed to try to get this right himself first. He could feel his walls starting to come down, his inhibitions lessening, and he wanted to keep his pride for as long as he could. Which, he realized, was impossible to do with the demon’s cock and fingers both inside him...so he guessed it didn’t really make a difference either way. He focused on the task at hand (or mouth), trying to make Crowley feel good, using his tongue and lips to try to copy what he’d had done to him over the years. 

 

“Mmm, that’s it, Dean. Be a good little whore for daddy.” Crowley said softly, and that made a big blush travel all the way down from the hunter’s neck to his ass, making the demon chuckle lightly. Dean surprised him by starting to grind down onto his chest, the motion making Crowley’s fingers sink in a little deeper and faster. “Oh, you like that, don’t you? Being called my little whore? And be careful, don’t want you cumming again so soon. You’ll be useless after.”

 

Dean forced himself to stop grinding, because Crowley’s words had started him on the path to blowing his load. Instead he lunged forward on the demon’s cock, gagging and trying to stay down despite it, hearing a loud and surprised moan from the man under him. He felt close to puking when he let himself come back up, gasping in a few gulps of air before Crowley’s hand went to his head and forced him back down, which made Dean’s cock shoot a little pre all the way down to the demon’s belly. 

 

“That was the halfway mark, Winchester, time for me to get off. I know you’re close, but you’re not cumming till I’m done, so this is going back on.” Crowley said, slipping his fingers out of Dean and the ring back around his member and balls, snapping it back snugly into place even as the man gagged on him again. “Now, if you don’t want me to fuck my load right into your belly, now’s the time to say so. Because I’m not stopping once I’ve started.”

 

“Water, please, Crowley.” Dean said, coming up with a gasp. He hadn’t had anything but a little booze to drink in hours, and his throat was getting dry. A warm bottle appeared in his hand, and he opened it quickly, gulping it down, as eager to keep going as Crowley. He threw the bottle on the ground when he was done, directing the mammoth cock to his lips. “Do it.”

 

Crowley surprised him by pushing Dean off of him, quickly getting off the bed. He looked down at the hunter with a smile, motioning for him to get on his back. It took Dean only a few seconds to get the message, and another few to work up the courage to listen to the demon, but just looking at that huge dick...he needed it. He flipped over and scooted back so his head hung over the bed, Crowley smirking down at him smugly. 

 

“Isn’t that a pretty picture? Now, I’m going to make sure you don’t throw up or...well, drown. The amount of semon I produce is rather generous. Otherwise I’m just going to give you everything I’d got. If you absolutely  _ need  _ me to stop, snap twice, loudly.” Crowley said, giving Dean a brief second to argue with anything before stepping forward, sliding his cock in a few inches and reaching a hand down to grip the Winchester’s throat gently. Dean’s rod leaked and jerked as Crowley slid forward, feeling his massive member stretch out the man’s throat.

 

“Oh yes, that’s much easier, isn’t it? This is going to be wonderful payback for all that annoying interference you and your brother seem to be so fond of.” Crowley said, grinning as Dean gagged at the eight inch mark, but he just kept pushing forward. The hunter’s hands went up to grip the demon’s thighs, but he didn’t shove Crowley away, letting him get another couple inches deep inside before he gagged more violently, his hips bucking upwards as the lack of air just aroused him further. “Though, I don’t think you’re supposed to enjoy me getting my payback so much.”

 

Ten inches seemed to be Dean’s limit for now, which Crowley was impressed by, especially when he started to pick up the pace and fuck the man’s throat. Every thrust made Dean’s throat slicker and more receptive to his prick, a combination of precum and saliva the perfect lubricant. The view was incredible, Dean’s body glistening and flexing in the firelight, his cock dripping so much there was a puddle forming on his soft abs. His hands were clamped on the demon’s thick thighs, sometimes pushing to show he needed some air, other times pulling and trying to take him deeper. Crowley felt the sweat dripping down his body, and he groaned as a loud choking noise came from the other man, the pressure on his cock incredible. He withdrew quickly.

 

“Deep breath, I’m going to cum soon, and I’m not stopping once I’ve started.” Crowley said, watching Dean gasp in air and stare up at him with pupils blown wider than he’d ever seen them, his face covered in spit and pre, and Crowley couldn’t resist bending down and shoving his tongue down the other man’s throat. Dean whimpered and kissed him back desperately, his sounds pliant and begging, all hint of defiance gone. When he finally broke them apart, Dean was panting. 

 

“Get it, Crowley, bust your nut. Cum in me.” Dean pleased, Crowley’s eyes widening, the demon wasting no time. He stood, sliding his cock back into the Winchester’s throat, watching it bulge around his massive dick. He immediately began thrusting into the wet heat like he was plowing a tight pussy, Dean’s hands flying back to his legs and trying to slow Crowley’s brutal assault, which did nothing against the demon’s strength. The poor man’s throat was being stuffed too full, but Crowley didn’t care. 

 

“You wanted my nut? You’re going to get it, whore!” Crowley shouted, grabbing the Winchester’s arms and pinning them to the bed, leaning over and spreading his legs, forcing his cock deeper, nonstop choking and gagging noises leaving Dean’s throat when he was allowed to get the tiniest bit of air. The demon felt his orgasm start to rise, his thrusting getting rougher, and he used a little demonic mojo just to make sure the man beneath him would survive what was about to happen. All twelve inches slammed into Dean’s gullet over and over, until neither man could stand it any longer.

 

“That’s it, take my cock, _ take it _ , yes!” Crowley screamed as he began to gush hot spunk down Dean’s abused throat, Dean’s eyes bugging out as he felt Crowley’s cock start to shoot like a firehose right into his esophagus. There was too much, which only made it hotter, and Crowley groaned as he saw the ring around Dean’s cock glowing, showing Dean was experiencing an intense orgasm even though it wasn’t allowing him to shoot. “Oh hell yes, cum on my cock you little slut!”

 

Dean was indeed, cumming on Crowley’s cock, every inch of his body electrified with pleasure as the ability to breathe was taken from him. He couldn’t stroke himself with Crowley pinning him as he yelled as cursed, but it was still one of the best orgasms he’d ever had, and still the demon pumped more and more semon into his gut. He could feel his stomach filling up, like he was chugging heavy, hot cream without stopping. His body shook as the demon’s orgasm outlasted his own by almost a minute, his weak attempts to start to breathe again finally noticed. 

 

“Almost...let’s have you taste the rest...” Crowley said, breathing hard as he started to slowly withdraw his foot long prick from it’s slick home. “Swallow it all first, you don’t want cum in your lungs. My power won’t let you suffocate.” he continued, his cock covered in his seed, still spurting every few seconds as his orgasm finally ended. He stroked his remaining load into Dean’s open mouth, watching the Winchester slowly swallow down what was offered, grinning as he saw the human’s middle looking a little pudgier than it had before, like he’d just eaten a huge meal. Or drank down the world’s biggest, hottest protein shake. He helped Dean get back up on the bed properly when he was done, the man shaking and hard, looking thoroughly fucked.

 

“Now, I quite enjoyed myself. How about you, Squirrel?” Crowley asked innocently, Dean lying back on the pillows, looking dazed and exhausted, his cock twitching when Crowley started rubbing up and down on his thighs. The demon got between them, running his hands over the other man’s whole body, admiring him and trying to help him relax. “You did all that with only a little help from me, I’m quite impressed. It’s like you were built to take cock.”

 

“Holy  _ shit _ , Crowley. That was...almost too intense. I feel like I’m high, or drunk. And I’m so  _ full _ , my stomach...how much did you shoot in me?” Dean asked quietly, his voice rough from the hard fuck his throat had gotten, rubbing over his belly and swallowing. It shouldn’t be noticeable when he went home, it just looked like he had a big meal. He hoped. His voice would be another matter.

 

“I told you, I’m quite productive. Most demons are, if you remember. But I seem to be rather more so than most. Especially when I’m with someone as tantalizing as you. You did enjoy all that, I assume?” Crowley said, smirking when Dean eventually nodded almost shyly, looking the demon up and down like was seeing him in a new light. Crowley leaned forward and locked their mouths together, loving how submissive and slick Dean was now. Eventually the hard cock throbbing against him got his attention.

 

“How about a reward for being such a good little hole for me, hmm? Let’s get that thing in my ass.” Crowley said, Dean’s eyes widening as Crowley slid up higher on his body, using the copious amounts of precum on Dean’s body to slick up the man’s cock. Crowley removed the cock ring, wanting the hunter to get off at his own pace. He didn’t give Dean a chance to argue or resist as he slid down, groaning and looking up to the ceiling of eight inches of heaven were slowly worked into him. Once Dean was balls deep inside, he looked down and smiled at the shocked and blissed out expression on the man’s face. 

 

“Oh god, Crowley, you feel amazing.” Dean said, running his hands over Crowley’s chest and stomach, groaning as the demon flexed his hole around him. “Ride me, come on, don’t tease. I know you’ve got a lot more stamina than me.” Dean pleaded, Crowley laughing, knowing that was Dean’s way of saying he was too exhausted to participate much.

 

Truth me told, as much as he had always wanted to fuck the hunter, riding Dean’s cock had always been one of Crowley’s favorite fantasies, and this lived up to the hype. He was so beautiful, making such pretty little noises and expressions as the demon lifted and lowered himself slowly, letting himself enjoy it. He stroked his huge cock lazily, knowing they both would get there eventually. 

 

“You’re so tight, don’t stop.” Dean begged, Crowley leaning down and sliding his tongue into his mouth, grinding himself down and closer to the Winchester, using his cock and stomach to give himself pleasure and causing the human below him to moan. Crowley just kept getting slicker as Dean slowly leaked more and more inside him. Dean broke off the kiss to gasp and throw his head back when Crowley took him all the way and squeezed. “Is there anything you need me to do?”

 

“Just tell me when you’re close so I can cum with you. Demons are very good at controlling our own orgasms.” Crowley said, Dean’s hands gripping his hips as he leaned back and used the hunter’s cock to hit his sweet spot. “A nice, thick cock in the ass definitely helps. One of these days I need to have you give it to me properly, show me that famous Winchester technique that has all the girls dripping.”

 

“I’m already getting close, god your voice is hot.” Dean admitted, thrusting up lightly as his orgasm neared, Crowley grinning and moving faster, jerking his cock in time with the other man’s thrusts. His own climax rushed up as he watched the expression on Dean’s face go from desperate to determined, the hunter pumping his cock faster and harder, his eyes squeezing shut and his mouth opening. “I’m gonna cum!”

 

Dean’s renewed effort was enough to push Crowley over the edge, the demon groaning loudly, both men throwing their heads back as they came as one. Crowley could feel Dean throbbing and shooting another load into him. He did his best to avoid the other man’s face with his own generous amount of cum, but a couple huge spurts made their way there anyway, covering the Winchester’s shocked face, chest, shoulders, and stomach. He was too busy pumping his load into the demon’s ass to complain, but at the end of his, he was panting and looking all over himself in surprise.

 

“Dude, you  _ just  _ came. How the hell did you shoot so much again?” Dean asked, Crowley just humming contentedly as he slid himself off the spent cock and flopped down next to the other man. He slid his hand across the smooth stomach of the hunter, letting the mess slide across his skin, Dean watching in a mixture of disgust and fascination. It should be gross, but he had already swallowed so much of the demon’s load, it was sort of hot. 

 

“This is only about half the size of one of my regular loads, Dean. Next time I’ll shoot it all over your face, and we’ll see if you still think this is a lot.” Crowley replied, Dean’s mouth dropping open. Crowley quickly slid his messy fingers inside, making the hunter gag and groan a little. Dean grabbed the demon’s wrist, but didn’t pull him away, slowly sucking on the fingers until they were clean, then removed them with embarrassment all over his face. “While I would be very happy to continue that until every drop in inside your adorable stomach, I think a shower might be a more effective approach. Agreed?”

 

Dean nodded, accepting Crowley’s help getting out of bed, his legs somewhat unsteady under him. Crowley proceeded to lead Dean into an opulent bathroom of white marble and gold veins. He tried not to think about how the floor he was walking on could be worth more than all the money he had hustled in his lifetime. And he was dripping demon cum on it. The shower he was led into could have fit half a dozen people...which was potentially the point, he realized. There were few words spoken between them as Crowley got the water hot, and proceeded to do most of the work washing the both of them, his fingers caressing and washing and touching and prodding, and Dean just...basked.

 

Intimacy like this was something he hadn’t gotten as often as he’d liked, except when he was with Lisa. Even then, this was different somehow, and Dean didn’t really want to think about why. But he didn’t complain when Crowley’s hands and fingers roamed long after they were both clean. Eventually, he started toying with Dean’s hole, making the hunter moan and put his hands on Crowley’s shoulders as their cocks rubbed together.

 

“I don’t think I can handle more tonight, Crowley. I feel like I’m about to fall over.” Dean said, the demon’s fingers not actually entering him, just spreading and rubbing and driving him a little crazy. “I mean, I don’t think I could stop you, but...” Dean said, giving Crowley the option to just take what he wanted. He was pretty sure he could handle it, maybe even cum again, but his level of participation had been fucked out of him when Crowley had fucked his throat like that.

 

“Mmm...tempting, but I think I’ll let you off the hook tonight. Assuming that this won’t be a ‘one time thing’ or some such nonsense? Are you finally done trying to convince yourself you don’t want this?” Crowley asked, his hands gently rubbing up and down the hunter’s strong back. It took Dean a solid moment of contemplation, but he eventually nodded, resting his forehead against the demon’s neck.

 

“Just...please don’t tell anybody. I don’t  _ like  _ wanting this so much, Crowley. I just can’t help it.” Dean protested, Crowley giving a little chuckle and turning the embrace into more of a true hug, both of them enjoying the feel of the hot water around them.

 

“It’s because of my ‘hot voice’, isn’t it? Would toning down the accent help? I could always try to pass for American.” Crowley said, Dean groaning in embarrassment and breaking off the hug. Crowley turned off the shower with a grin, getting towels for the both of them. “I won’t tell anyone, Squirrel, but you really have nothing to be ashamed about.” 

 

“The day I tell the world I like dick is the day you and your lackeys take up hunting.” Dean said, toweling himself off, not noticing the glint that appeared in Crowley’s eyes at his words. “So...how are we gonna do this? I mean, I don’t know how I feel about being a demon’s booty call. I have a life, and cases, I can’t just drop everything when we wanna...you know.”

 

“We’ll play it by ear for now. It’s sex, Dean, and we’re hardly a married couple several decades deep. We don’t need to schedule it as some grand event. You just let me know when you’re getting a little antsy, and I’ll help...relieve the pressure.” Crowley promised, leading a now dry Dean out of the bathroom with a hand on his ass. “Next time, I may have to get inside you...you have any problem with that?”

 

Dean just shook his head and blushed as he started getting his clothes, Crowley just watching him dress. He didn’t get the whole awkwardness humans got when they were finished with sex, even with his slightly more human nature. He stayed naked as Dean put on his layers, the hunter’s eyes staying glued to the ground. He finally got some eye contact when the other man sat in his chair to put his shoes on.

 

“God, do you have to look at me like that?” Dean protested half heartedly, but his eyes didn’t leave the demon’s as he finished with his shoes, getting up slowly and walking over to him. 

 

“I prefer ‘Crowley’, or ‘my lord’, especially since we’ve both met the Big G in person. But, yes, I do. You’re quite fetching in the firelight. At some point I might look for a painter in the pits, see if any of them could do you justice.” Crowley said, sliding his hands under the man’s shirt and rubbing them up and down, knowing they both were thinking about just how full the Dean was of his seed.

 

“Yeah, sure, whatever floats your boat...I’ll see you later?” Dean asked, Crowley’s mouth on his all the answer he needed. The kiss grew deeper, both men groaning, and Dean had to push the demon away. “Alright, I’m...I’m gonna go before...yeah.” he said nervously, his cock half hard in his jeans. Crowley was at full attention, and he was about ten seconds from dropping to his knees and begging for some more rough treatment. He almost ran to the door, shutting it behind him even as he heard the demon laughing, and didn’t relax until he was safely back in Baby.

 

He was fucked.

**Notes for the Chapter:**

> By all means, comment on what type of things you might like to see happen, or pairings everyone likes. This will eventually be Dean/Everyone, for the most part.


	6. Some Soul Swapping

**Summary for the Chapter:**

> Crowley's come up with a plan, but sadly needs a little help to bring it to life. Thankfully, he has a Nephilum who owes him. Mainly plot here!

~~~~

Crowley walked amongst his lackeys, the ones he  _ thought  _ were the cream of the crop, and scowled. Injuries everywhere, only some looking like they could have been fatal to humans at least, but it was much less than the demon had hoped for. He stopped at Antonio, looking him up and down, pleased to find him without any marks...at least until he turned around and lifted his shirt, revealing a long scratch on his back of otherwise beautiful copper skin.

 

“We weren’t expecting their numbers, my lord. I’m sorry. I take full responsibility.” Antonio said, lowering his shirt and turning back to Crowley, his eyes on the floor. He looked rather ashamed, this being the first time he’d ever come back with anything less than a perfect performance. The king of hell took a deep breath, looking at all the others, who all equally avoided his gaze. 

 

“No, the responsibility is mine. I thought superior strength and weapons would be enough, but apparently we’ll need more expertise than I realized. Bloody vampires. All of you, get out of my sight and get cleaned up. This was a test run, there will be no excuses next time. Understood?” Crowley said, everyone murmuring affirmatives and slinking away, but the king grabbed Antonio’s well defined bicep before he could run off.

 

“Not just yet. I’d like to take another look at that cut...it looked rather serious.” Crowley said, Antonio looking greatly confused for a moment (a scratch like that? Serious to a demon?) before realizing what Crowley meant with a smile, stripping off his shirt and turning around. Crowley worked his fingers over the cut, muttering and healing it with a simple spell he’d learned. “I have ideas on how to get the help we need. You won’t be going in as blind next time, if it all works out the way I’m hoping.”

 

“Do you need any help with any of it, my lord?” Antonio asked, stretching and feeling the newly healed area tingle slightly. “Anything at all?” he continued, turning around and slipping one hand a little into his waistband, knowing he looked...rather alluring, at least to most. Crowley smiled, running his hands up and down the other demon’s torso, causing the younger man to let out a soft sigh.

 

“Not quite yet, I have a Nephilum to deal with. But I will be asking Dean if he’d like you to join, once he’s a little more comfortable. Until then...perhaps tonight, when I’m back, you can meet me in my chambers for a...debriefing.” Crowley said, hooking a finger from each hand in Antonio’s belt loops and bringing him closer, the other demon’s eyes going black with desire. “If you have no opposition? We may need to work some very  _ long  _ hours.” 

 

“I’ll prepare myself for some very strenuous...debriefing, Lord Crowley.”

 

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Crowley sipped at his rather delicious Italian coffee as he put down his phone, looking over a beautiful sunrise. He had acquired the expensive villa only a few weeks prior, but it was quickly becoming one of his favorite relaxation spots when he could pull himself away from Hell. He leaned forward to pour more of the hot drink into the second cup on the table as he heard the telltale sound of angelic wings.

 

“I’m grateful you could be so prompt. Did I wake you? I know Nephilum don’t require quite as much sleep as humans, but I hope I didn’t disturb your napping.” Crowley said to the newly arrived Jack as he finished pouring. He was wearing jeans and a simple white t shirt that fit him snugly. The Nephilum was looking around with awe at the beautiful place he’d shown up in, night turned to day in an instant, giving him a beautiful view of the Italian countryside as the sun rose. 

 

“What? Oh, no, I haven’t gone to bed yet. Castiel thinks I need to sleep about half as much as humans do, and that I can go without that if I want to. But I haven’t tested it yet.” Jack explained, walking over to the edge of the balcony and looking down at the beautiful stone courtyard and impeccably well kept garden. Crowley noted that he was barefoot. “What is this place?”

 

“Just a little spot to relax, take care of some more delicate aspects of my work, as well as something to use as a reward for those who please me. A lovely place, with a lovely amount of uses.” Crowley said, looking the young man over. He really was something, the beauty of both humanity and angels practically shining through him. Crowley knew he was the reason for his slightly more human nature, which he couldn’t help but be a little grateful for. “Coffee?”

 

“Sam and Dean say caffeine makes me even more energetic than normal.” Jack said, turning back to Crowley and peering at the already poured cup with a small frown. He had drank soda before, even an energy drink once, but never coffee. 

 

“Well your daddies aren’t here now, are they? Or are you required to do every little thing they say?” Crowley asked, a challenging eyebrow raised. Jack shifted his weight from foot to foot a couple times, before walking over and picking up the offered cup, sniffing curiously before taking a small sip and making a grossed out expression. “Perhaps a little cream and sugar? Coffee, even the best, which this isn’t, can be a bit of an acquired taste.”

 

Crowley poured some of both into Jack’s lowered cup, stirring it with a spoon and allowing the youngest Winchester to taste it once more. The Nephilum smiled after, taking another sip, and sat when Crowley waved his hand at the chair across from him at his tiny tea table. Jack poured a little more cream in before seeming satisfied, looking at the view with a smile.

 

“It’s a very beautiful place. But...your text wasn’t very clear, why did you want to speak with me? Is this about what I owe you? Because I do want to repay you for helping us. I don’t know how we would have gotten out of such a difficult situation without you.” Jack said earnestly, which made Crowley giddy on the inside. The most powerful being presently in existence, eager to help him. He took a deep breath, knowing he could very easily regret it if he abused the offer in any way. The old Crowley might have done so...but his new humanity had given him new insight.

 

“It is, in fact. I’ve heard you’ve been doing well with your lessons, haven’t you? Been learning a lot about how the world works, culture, mathematics...hunting. All sorts of things.” Crowley said, Jack looking a little confused, but nodding. 

 

“Yes, everyone’s been teaching me a whole bunch of stuff. Sam says he’s running out of math that he’s able to teach me, and that he’s having to do way more research than he thought just to come up with my homework. He doesn’t seem to mind too much, but I’m hoping they’ll let me start with online classes soon, so he can focus on organizing the hunters. He seems to really enjoy that.” Jack replied, Crowley smiling and finishing his cup before setting it down, folding his hands and putting them on the table.

 

“Do you ever wonder, Jack, what their lives might be like if they didn’t have to hunt? If there was someone else to take over that responsibility and let them have lives and jobs that were a little more...shall we say, normal?” Crowley asked, and Jack looked contemplative as he considered his words. He really was extremely attractive, the things the demon could do with him...

 

“Mary has talked to me about that, a little. She said she never wanted them to be hunters. They’re really good at it, everyone knows that, but...I guess it would be nice if they could just do whatever they  _ wanted  _ to do instead. Dean’s really good at driving and fixing cars, and Sam’s super smart about a lot of stuff, so maybe he could be a teacher? I know Mary has told me I don’t have to be a hunter, Castiel too, but it always seems like they don’t feel like they have a choice.”

 

The young man was practically repeating the script that Crowley had written for him in his head, and he had to restrain himself from grinning or even applauding. The demon got up, walking towards the balcony with his hands clasped behind his back, giving Jack a chance to think on his words and wonder why he was being asked such questions. 

 

“What if I told you that I had an idea that might allow such a world to exist, and that it would be, at least party, a way for you to repay the help I’ve given to you all at the same time?” Crowley said, and he heard Jack get up and join him, but kept his eyes forward on the horizon. “You have some very unique skills, Jack, ones that would be incredibly useful to my plan. What do you know about Hell, and demons?”

 

“I know that most of them are evil, and that...well, they say I shouldn’t trust you too much, even though you’re one of the better ones. That you might have ‘ulterior motives’.” Jack said, Crowley nodding in agreement. “Demons are humans who have been stripped of their humanity by torture from other demons, except for the first ones who were...tortured by my father. And they want to bring more souls into Hell, right?”

 

“That used to be the case...and so far as ulterior motives, I won’t lie and say that I don’t have any, but none that will cause any harm or unhappiness to you or your family. Demons used to be at war with Heaven, you see, and more souls equalled more power. But, as I’m sure you know, there aren’t exactly armies of angels waiting to take down our gates anymore. So what motivation would I have to increase the armies of Hell if there’s no one to fight?” Crowley said without deception. He had already had to explain this plan to his elite demons, which had been a hard fought but successful debate. Demons not conquering? A difficult concept to swallow. 

 

“Huh, I never thought about that. Hell is where all the bad people go, right?” Jack asked, looking confused. Crowley had a feeling the Winchesters hadn’t gone into extraordinary detail over Hell, at least not yet. They seemed to be focused on his regular education more than hunting training lately, which just made things easier for Crowley. And he didn’t even have to lie.

 

“Yes, and it used to be that the masses needed ‘attending’ by other demons as a way to convert them into more of us. But not only are more demons unneeded, my Everlasting Line method of torture means that we need, at maximum, several hundred demons to be monitoring their imprisonment. The benefits of having someone who thinks of more than fire and brimstone in charge.” Crowley said, rather pleased with himself. Really, he was shocked that no one had thought of it before. Waiting in lines with no forms of entertainment was one of the worst experiences in the universe. 

 

“Well, it sounds like you’ve got everything under control. So, what do you need my help with?” Jack asked, finishing his coffee and making the cup float over to the table, setting it down with a small clink. Crowley wondered how the Winchesters and their lot were training the boy to use his powers, and just how strong he could become. Stronger than an archangel...there was potential there.

 

“Yes, onto business. Well, seeing as Hell’s purpose is very much in question, I thought we might try our hand at the hunting profession, in addition to our usual offers of souls for services rendered. Demons like violence, and dislike being trapped down below, so the chance to take down monsters up above could be a good incentive for those under my charge.” Crowley said, letting himself sound casual, knowing if any of the more experienced members of Jack’s family were here they would likely scoff and immediately doubt the remote possibility of this being possible.

 

It had taken a lot of convincing, but Crowley had picked his new top demons carefully, looking for qualities that previously he had seen as weakness or problematic. Innovation, people who thought outside the box instead of whichever box he told them to think inside of...independence. The difference being that he had to earn their respect more than any under his command previously before their loyalty was assured...but once they saw they weren’t dealing with a mindless brute, getting them to listen to his new and dangerous ideas had become possible. The old ways were clearly not working well, for demons or humans, and changes needed to be made, something Crowley was more than happy to help orchestrate. 

 

“Hunting? I didn’t think demons could do that. Or, would, I guess. Dean seems to think that most of you are pretty evil.” Jack said, frowning, before looking at Crowley as if he’d realized he’d said something potentially offensive. “Not that he talks that way about you, he seems to like you a lot better than other demons.”

 

“If only you knew how much better. But my demons will do whatever they are commanded to; if I command them to hunt, then hunt they shall. It won’t be hard to motivate them, a successful hunt will not only mean time above ground and sanctioned violence, but other potential rewards. Gone will be the days of demons getting their positions from age or your father’s favor. I look for results.” Crowley said, leaning on the railing and smiling at the sunrise.

 

“That does sound like good motivation...but where do I come in? I don’t know much about hell, or demons.” Jack asked, still looking confused. Crowley wondered how much they had taught the young man about sex...and how upset the Winchesters and Castiel would be if their Nephilum was returned to them covered in demon spunk.

 

“Something you’ve done before, more or less. Opening a rift to the Apocalyptic world...and retrieving a soul or two that reside in the afterlife there.” Crowley said, and Jack’s eyebrows went up in surprise. “Allow me to explain. I require the services of one of your best, Robert Singer, to train my demons as hunters. Now, the old me could have gone about this via threats or kidnapping, but I’m a changed demon. I know the only way to keep the Winchesters and their gang on my side is to play nice. And what could be nicer than returning Bobby’s wife and child to him in this world?”

 

“So, I would just be...taking their souls from that Heaven, and bringing them to this one?” Jack asked, Crowley nodding. “But I’m not sure how, and I had help the last time I opened a rift. I’m not sure I’d be able to do that again.” he continued, looking uncertain. Crowley placed a hand on the boy’s shoulder, gripping it lightly and smiling. The boy had more muscle than he’d realized.

 

“You opened that first rift when you were nothing more than a baby, not even born yet. I have no doubt you’ll be able to do so again. You’ve improved quite a lot, I’ve heard. As for retrieving their souls, I have that part covered. Between the two of us, it should be no problem.” Crowley said, Jack slowly nodding as he listened to him, a frown on his face. He looked down at Crowley’s hand, and when his eyes returned to the demon’s, they glowed brilliant gold.

 

“I want to help you, to repay you, but I need to be sure. Too many people have tried to abuse my powers. Are you hiding anything from me? Are you planning on betraying or hurting my family?” Jack asked, Crowley too surprised to remove his hand in time as golden light crackled through his skin, the powerful grace of the Nephilum filling him and forcing truth from his lips.

 

“In addition to gaining someone to train my demons, I wish to use the rift to recover artifacts and treasures that have been lost in this world, that may still remain in this one. I don’t wish to use any of them to harm you or your family without provocation, merely as a means to assure myself and my rule will be protected. I also wish for the old Bobby Singer of this world to be returned to Earth from whatever prison Heaven has him in, while the soul of the other Bobby will split his time between training my demons in hell and staying with his wife and son in Heaven. I liked Bobby, and it would all but cement the Winchester’s gratitude and loyalty to me.” Crowley said, unable to stop himself, wishing he’d had Antonio or someone else accompany him. But he didn’t think there was anything in his plan the Nephilum would disapprove of...he hoped.

 

“Is that all? You don’t wish to abuse my powers, or use me?” Jack asked, and Crowley really wished he hadn’t phrased it like that. Thoughts of what he really wanted to do to the young man sprang into his head despite his resistance.

 

“Not your powers, but  _ you, _ yes. I want to strip you bare and see just what Lucifer’s son is packing, show you just how outstanding sex can be. I want to bend you over this railing and pound away at your ass with my cock, to make you beg for it and scream my name. I want to-” Crowley stopped as Jack backed a few steps away, his power leaving the demon and making him grasp the railing to keep from falling over. That had not been part of the plan.

 

“You...what? You want to have sex with me?” Jack asked, looking much less intimidating than he had a moment before, his face red and his stance vulnerable. Crowley shook himself, clearing his throat and adjusting his tie. Jack looked around like he was afraid someone was listening, but Crowley had made sure their meeting would be secret. 

 

“Of course I do, Jack, look at you. You’re quite a good looking young man, and all that hunter training is keeping you quite fit. It would be an honor to partake in...festivities, with you. But that’s one reason you should be careful forcing people to be honest, you might not like what you hear.” Crowley said, trying to maintain his composure. At least he hadn’t said anything that had indicated any foul play on his part. Not that he was planning on any, but one never knew.

 

“Sorry, I had to be sure you weren’t...you really want to have sex with me? I’ve never had anyone say that before. I haven’t even done it before, and Dean  _ still  _ hasn’t asked Cas about teaching me about sex.” Jack said, almost to himself, the image of Castiel giving it hard to the Nephilum a delightful image Crowley would save for later. Perhaps they could all take turns teaching the boy.

 

“Well, regardless of our business with souls and rifts, if Dean or Castiel don’t end up teaching you about sex sometime soon, I would be very happy to take on the responsibility. Demons know an awful lot about sex, after all, myself more than most.” Crowley offered. Jack just looked at him with a slightly open mouth, and the demon was quite certain the young man was aroused by the idea...but that could wait. “Now, about our other business?”

 

“Right, sorry...where do we start?”

  
  
  


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After a couple hours of preparation and teaching on Crowley’s part, and a lot of squinting and concentrating on Jack’s, a rift had been successfully opened. Crowley summoned a reaper, a parallel version of one he had dealt with for many years in his world, who was thankfully still alive. It took another hour or so, during which time Crowley and Jack went to retrieve a few well hidden artifacts, but the two souls of the family this world’s Bobby held dear were soon in Crowley’s possession. It took almost a half hour for Jack to close the rift he had opened, but eventually it sealed itself with a snap, a tired looking Nephilum smiling weakly at him.

 

“Well done, Jack. I know a lot of this is new to you, and your help is appreciated.” Crowley said, looking at the two small jars and the souls they held. Karen and Daniel Singer. He couldn’t wait to see the look on Bobby’s face. He had little doubt the hunter would choose to go to Heaven with them, especially since his counterpart that was already up there was likely eager to get out of the prison the angels had him in. Now that the angels were so few, Crowley’s information gathering was all but unopposed, and even many of Heaven’s secrets were open to him.

 

“I’m glad I could help, but I should probably be getting back. When are we telling Bobby?” Jack asked, wiping the sweat off his brow and breathing a little hard, like he’d just went on a jog. His shirt was clinging to him in a lovely way, but Crowley forced himself not to travel down that road yet.

 

“As soon as I ask my mother about a spell to swap two souls from Heaven to here. Normally, when a soul is in Heaven, it stays there. But since they’re practically the same person, a swap should be much less likely to set off any alarms. Go home and rest, I’ll call you once I have the spell. It’ll be a grand little reunion for everyone, and I’ll have someone that can teach my hellspawn how to outwit a werewolf.” Crowley said, smiling at Jack, who shuffled his feet.

 

“About...about what you said earlier. If none of the others want to teach me about sex soon...would you? I really want to know about it, how to do it, how it feels...all of it. I don’t know if the others are willing to, they just see me as a kid sometimes. But you...don’t.” Jack said awkwardly, Crowley’s brows going up and a smirk coming across his face.

 

“It would be my absolute pleasure. Yours too, if I have anything to say about it. I won’t tell anyone, if you keep quiet about all this until everything is ready, and about what I’m requesting from Bobby as payment. I know the Winchesters don’t fully trust me, which I suppose I can’t blame them for. But you  _ know  _ I’m telling the truth, and that this will be beneficial to everyone. I get a drill sergeant, New Bobby gets his family back, Old Bobby and the Winchesters are reunited. Everyone wins.” Crowley said, thrilled with the idea that he might be the first to ravish the young man, but attempting to stay on task. He was going to need to bang the hell out of Antonio when he got back down below. 

 

“Of course, it will be a surprise. Thank you, Crowley...for believing in me. Do you think, maybe, I could visit Bobby when he’s down teaching in hell? I don’t know the Bobby from this world, but the one I do know has been really nice to me.” Jack asked, looking a little sorrowful. The son of Lucifer in hell felt a little too fitting, but staying in his good graces was on the top of Crowley’s to do list. Plus, having the Nephilum at his side would likely only solidify his rule. 

 

“Any time you wish, Jack. Just say the word. Now, go get some sleep, you look exhausted.” Crowley chided, the young man nodding and smiling, before disappearing in a rush of wings. The king of hell resolved to have the Nephilum screaming and begging for more underneath him as soon as possible. Until then, he had some souls to store safely away, and a gorgeous Latino demon to worship in his bed. 

 

______________________________________________________________________________

  
  
  


The idea was accepted about as well as he thought it would be. Winchesters left and right yelling about what he could be trying to pull, who the hell did he think he was (the King, thank you), and why hadn’t anyone been consulted, why had Jack been brought into this...through it all, Bobby just stared at the two jars Crowley had placed reverently on the table in silence. Rowena stood next to her son, the two of them patiently waiting for the shouts to die down before speaking, but Bobby beat them to it.

 

“Is that really them? Karen and Daniel?” Bobby asked, almost in a whisper. Castiel walked over to the two jars and placed a hand over them for a moment, then nodded to Bobby, but didn’t look any happier about the situation than anyone else. “...I’ll go with ‘em.”

 

“Bobby, think about this. Is this really what you think they would want? For you to give up the rest of your time on Earth to be with them?” Mary asked, a hand on his shoulder, though she looked like she wasn’t really sure of the words she was saying, thoughts of John and what she would do if all of her family was waiting for her in Heaven flashing through her mind. Bobby looked at her with a weary look on his face.

 

“You all know how much I’ve grown to like you all, to respect you...but I’m not the same guy you know. I didn’t raise these boys, I didn’t grow up in this world. I went through a war that sucked the life outta me, then got a second chance at life over here...and you know what? I would give it all up to hold my wife and my boy in my arms again for just a few seconds. And I dare each and every one’a you to say you wouldn’t do the same in my shoes.” Bobby said, looking around at all the faces around him. Even Dean, full of anger at having this sprung on him, deflated. Mary gripped his shoulder a little tighter, then nodded.

 

“We’ll miss you, Bobby.” Mary said, bringing him into a hug, the old hunter closing his eyes and sighing. Handshakes were had all around, except by Jack, who rightfully insisted on a hug. The Winchesters were conflicted. If this worked, they had Their Bobby back, but they were still saying goodbye to a friend. Sam and Dean both thanked Bobby for all he’d done for them, and he to them, but eventually Bobby took a deep breath and came to stand by the jars.

 

“We will need to go to the Gates of Heaven for the spell to have the greatest chance of success. Are you ready?” Rowena asked, a spellbook tucked under her arm. Bobby looked around at the room once more, a smile on his face, before nodding. Crowley whisked them all away to the park where Heaven’s portal resided. The smile on Bobby’s face disappeared.

 

“Alright, ya smarmy bastard, what do you want? And don’t give me any of that horse crap about ‘trying to prove that I’ve changed’. Your kind don’t do nothin’ unless there’s something in it for them. I’ve dealt with plenty of demons in my time, and charity work ain’t in your nature.” Bobby said, Rowena hiding a smile while Crowley just stared at the hunter in bemusement. 

 

“Right to the point, you really are Bobby. Well, for your information, I  _ have  _ changed. I’ve gotten smarter, and I’ve seen where the world is heading. If demons don’t change the way we do business, some new big baddy or apocalyptic event is going to come around, and we’ll get wiped out. Or at the very least, I’ll get overthrown. Do you know how many rulers hell has had this past decade? Too many.” Crowley said, Bobby folding his arms and looking at the souls of his wife and son impatiently. 

 

“Apologies, I’m stalling your reunion. What I want from you is...one year. One year of splitting your time between Heaven and Hell, half your time with your family, the other half teaching my demons how to properly hunt monsters.” Crowley said. There was a solid minute of silence...and then Bobby started laughing. A low chuckle at first, but it got louder as time went on, Crowley looking upwards and begging a god he was pretty sure wasn’t listening for patience.

 

“You want me to teach a bunch of scum sucking hellspawn, how to hunt...what, vampires? Werewolves? Maybe shapeshifters? You pulling my leg?” Bobby asked, and Crowley sighed and pulled out a contract, unfolding it and handing it to Bobby, who read it over, occasionally chuckling. “No torture...twelve hours...aren’t these things normally longer?”

 

“Simple contract for a simple man. But if there’s anything you wish to amend?” Crowley asked sarcastically. Bobby read over it once, looked up at the souls of his family, then read it over again. “I did my best to make it fair. One year of service for an eternity of familial bliss seems rather in your favor to me.”

 

“...no double cross? You’re not going to try to use any of the stuff I teach you to wipe out hunters or nothin’?” Bobby checked, looking like he wasn’t the happiest about this, but his eyes wouldn’t stop going to the jars. Rowena appeared to be casting some sort of spell, but other than a tingling sensation down his neck, Bobby didn’t pay her any mind.

 

“We don’t need much of your FBI knowhow or how to properly wear flannel. They just need to know how to kill monsters without collateral damage or being noticed. Demons are not known for their subtlety. You teach them to wipe out the boogeyman for a year, which starts after you get a few weeks with your family, and I’ll consider the debt of my assistance in all this repaid.” Crowley said, Bobby staring at the pen that was now being offered for a moment before taking it, rereading the contract  _ again _ , and signing. 

 

“There now. I’d offer a kiss to seal the deal, but your wife is present. Speaking of which.” Crowley said, Rowena setting the jars down and chanting a spell before lifting them up, the souls swirling around for a moment before a purple haze overtook them. After a moment, the form of a kind looking woman and a handsome young man appeared before Bobby, who’s knees nearly gave out. “Quickly, take their hands. They’ll lead your soul up, and help make the path for the other you back down.”

 

“Karen...Daniel...” Bobby whispered out, hardly able to believe his eyes. He reached forwards and clasped the hands of the two confused looking spirits, their blue light spreading to him. Once they realized who it was, both spirits smiled, and all three Singers began to rise into the air, leaving Bobby’s body to be caught and held up by Crowley as Rowena began to cast her spell. A purple trail was left behind the three, lingering long after the spirits had vanished. One minute passed. Then five. Crowley looked at Bobby’s body with impatience and a bit of worry.

 

“What’s going on, mother? Shouldn’t he be here by now?” Crowley asked, Rowena pursing her lips and shooting him an annoyed look. The purple trail she’d left for the Bobby of this world to follow was holding, and Crowley’s surprisingly detailed information about Heaven’s layout should have given the spell the accuracy needed to reach the old hunter. Even so...

 

“It’s a homemade spell, Fergus, and I  _ told  _ you there’d be no guarantees. This hasn’t been done before. I had to change the vessel so none of the previous host’s memories would overlap, otherwise we’d have a mismatching set of brain and soul to deal with. And that’s no bloody fun for anybody, let me tell you, so hold up the old coot and be patient. We just have to hope for the best.” Rowena argued, looking up towards Heaven herself with worry. She wondered if she’d ever get the chance to get up there, or if she’d have to attempt to remain immortal forever to avoid the Pit.

 

It took another ten minutes before the purple trail flashed and flickered, a bright and shining soul quickly making its way down like it was running from an angry hellhound. With a burst of energy that made Crowley’s hair stand up a bit on end, Bobby Singer breathed in his first earthly breath in many years, looking around in bewilderment before realizing who was holding him.

 

“Hello, Bobby Dear. Been a minute, hasn’t it?” Crowley said, Bobby shrugging him off and standing a few feet away, gazing up at the fading purple light of the spell. He glanced back down at Crowley, then Rowena, looking her up and down uncertainly. Crowley just smirked at the other man’s confusion. He’d always had a bit of a soft spot for the hunter. “How were the Pearly Gates, everything we’ve heard and more?”

 

“Not as nice of accommodations as I was expecting, least not since I helped the boys from up there. The hell is going on? Am I really...back?” Bobby asked uncertainly, shifting his feet around and stretching a bit, getting used to having a physical body again. “I feel...different. My back doesn’t hurt like it used to, but my knee’s killin’ me.”

 

“Different body, different injuries. I’m sure one of the angelically gifted members of your little club will be happy to help you out with that. You’re currently in the body of another Bobby Singer, from another world. Freely given, you can rest assured; he’s now finally with his family up in the big Halo Factory in the sky.” Crowley said, Bobby just staring at him like he was trying to see if the demon was pulling his leg. Bobby’s eyes wandered to Rowena.

 

“He tryin’ to pull a fast one on me? Who’re you supposed to be, a demonic secretary? She seems a little out of your league, short stuff.” Bobby said, Rowena smiling demurely at the flattery even as Crowley glared at the hunter.

 

“She would be my  _ mother _ , you ungrateful little-”

 

“Now, Fergus, let’s not be rude to the poor man. He must be terribly confused by all this. Why don’t we head back and let the Winchesters see their long lost father figure?” Rowena said, coming over to Bobby and holding her spellbook against her chest like a high schooler with her schoolbooks. “And I’m no demon, Mr, Singer, but the most skilled witch of this age, if I do say so myself. I don’t know all the details, but a lot has changed since you’ve been gone.”

 

Crowley bristled, but came over to the two of them and tried not to focus on the fact that Bobby seemed to be showing her quite a bit more interest than the previous version of him had. He reminded himself of how grateful Dean would likely be, and how much he was going to enjoy that heaving, sweaty gratitude the first chance he got. In a flash, they disappeared, and the Bobby Singer of this world entered the Bunker for the first time.

  
  
  


 


	7. Welcomes and Wagers

**Summary for the Chapter:**

> Bobby is welcomed to the Bunker, and Crowley wants a phone call with his Squirrel.

**Notes for the Chapter:**

> Sorry it's short, I'm sick presently and wanted to get this out while I had the motivation! Not much porn, this whole thing is gonna be a weird mix of porn and plot...hopefully y'all like it anyway!

“The son of  _ who  _ now?” Bobby said, looking at Jack with wide eyes and a disbelieving look. All three Winchesters had similar grimaces on their faces, Mary standing behind Jack and putting a hand on his shoulder while her two sons attempted damage control. Castiel sat next to Jack, staying close for emotional support if needed. Jack just stared at the map table, looking like he was trying to blend into the scenery. 

 

“Now, Bobby, I know it’s a lot to take in, and we’ll explain everything, but just remember who you’re talking to. Lucifer’s true vessel? And his older brother: Michael’s true vessel? Jack didn’t have any more say over anything than we did.” Sam said, leaning forward at the table almost protectively, but Bobby just scoffed and waved his hand at Sam.

 

“It ain’t  _ that _ , I’m just surprised that asshat could find anyone willing to shack up with him. Assumin’ it was willin’ at all. Think we learned a long time ago not to judge anyone on where they come from or who their parents are.” Bobby said, still looking Jack up and down with surprise in spite of his words. “Scared to ask, but where is the mom in all this?”

 

“He tricked her. My mother, I mean. He was possessing the person she was in love with, and...well...I happened. She was a beautiful person, so kind...but humans can’t survive giving birth to Nephilum. We met for a while, though, in heaven. Castiel says I can try to visit her again sometime, once he can be sure the other angels won’t try to use me for my power.” Jack said, Bobby still looking dumbstruck as he tried to process everything.

 

“We gotta lotta crap to explain, Bobby, but plenty of time to do it. Most important thing right now if that you’re back. How about I grab us a few beers, and we start swapping stories?” Dean suggested, still reeling from this whole thing. Bobby was back,  _ their  _ Bobby. Not that he wouldn’t miss the other one, but this was the guy who raised him and Sam, who pulled their asses out of the fire more times than he could count.

 

“Better bring some whisky too. I get the feeling it’s gonna be a long day.” Bobby said, taking off his hat and running his hand through his hair as he looked up at Mary and smiled, chuckling when he looked over at Sam. “I’m gone for how many years, several apocalypses have come and gone, your mom’s back, you’re raising Lucifer’s son, and you still ain’t cut your damn hair?”

 

There were laughs all around the table as Dean left to get the beer, Castiel’s eyes following him with a smile, a pleasant warmth running through the hunter’s body as he walked to the kitchen. His phone went off as he opened up the fridge, a short message from Crowley popping up when he unlocked it.

 

_ Call me later. _

 

Dean closed his eyes and took a deep breath, knowing he owed it to the demon. Knowing he owed a lot to the demon...but wanting to focus on his family for now. He grabbed as many beers and drinks as he could carry, and marched his way back to his waiting family. Hours passed, updating each other, reminiscing with one another. Drinks were shared, pizza was ordered, tears were shed, and smiles were worn often. It was close to midnight when everyone without angelic grace started to feel their eyes droop, and they set Bobby up in his alternate version’s room. Hugs were given, and all wished one another goodnight (after some final hugs, of course).

  
  


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“It’s about time, Squirrel. Demons aren’t supposed to sleep, but I still nearly nodded off waiting for you. Was it a nice family reunion? Mother and I figured it would be better to leave you all to it.” Crowley said, flipping through the pages of the novels Chuck had written on the boys. He’d already read them through a time or two, but refreshing one’s memory was never a bad idea.

 

“Yeah, yeah it was...” Dean said, letting out his breath in a huff and trying to choose his words carefully. He paced back and forth in his room, keeping his voice low. “Look, before I do any thanking, I gotta ask something first. You got another motive here? Is there some scheme you’re trying to work into this? Because, gotta tell you Crowley, this screams ‘distraction’ or ‘blackmail’ or something, and I need you to be honest with me, man. ‘Specially with what we’ve...with what’s been going on lately.”

 

“Of course I have ulterior motives, Dean; I nearly always do. But you’ll be happy to know that my other motives have nothing to do with hurting you, your family, or any random passerby on the street. As a matter of fact, I do believe they’ll help humanity at large. But before you ask, no, I won’t be divulging any of my secrets at this time. Wouldn’t be much of a king if I couldn’t keep my mouth shut...well, mostly shut.” Crowley said, and he could feel the weight of his words through the call. Dean stopped pacing, shutting his eyes.

 

“Thanks. For Bobby, thank you. I didn’t think Sam and I would see him again till we croaked, if even then. He said he was stuck in some Heavenly jail for helping us, not sure he would have gotten out if it wasn’t for you.” Dean said, knowing genuine thank you’s weren’t really their thing, but feeling one was necessary here. There was silence on the other end of the phone for a bit.

 

“If course, Dean. I’m happy to help. Now, that being said, there is one ulterior motive I’m willing to tell you about...” Crowley said, and Dean felt a familiar pull of arousal from within him at the change in Crowley’s tone. “I like a grateful Winchester. I’m interested to see exactly how grateful you can be. What say you take a little trip over in my direction, and we’ll find out together?”

 

Dean forced himself to breathe normally, unable to stop the images flashing in his mind. Crowley lounging in nothing but a robe, the demon naked and hard above him, filling and pumping and sucking...he could be very, very grateful to Crowley. On his knees, on all fours, on his back...he shivered and swallowed, keeping his voice even.

 

“I’m not saying no, just...not right now. Bobby’s here, and I feel like I should take a few days to focus on my family, if...if that’s alright with you?” Dean asked, realizing that he was essentially asking Crowley’s permission. He was the one that brought Bobby back to them, with Jack’s help. If the demon demanded he come and service him immediately...Dean wouldn’t have a hard time saying yes. Crowley hummed on the other end of the phone, stroking the bulge in his tailored pants.

 

“Very well, I can be patient. But be honest, Dean. You’re just using this as an excuse to finally get some alone time with that angel of yours. Not that I’m jealous; on the contrary, I think it’s about time that angel got a nice throatful of something.” Crowley said, touching himself idly and enjoying the thought of Castiel gagging and sputtering on Dean’s dick. Dean opened his mouth to retort, or defend Cas, but stopped and shook his head. He thought about all the angels and demons who had made jokes or statements over the years.

 

“Why do you and every other supernatural pervert keep making comments about Cas bangin’ me? Guy’s about as straight laced as they come, he’s only ever banged women. Well, woman. Even then, he was human. Don’t really think Cas is interested much in bumpin uglies.” Dean said, frustration in his voice. For a moment, Dean thought Crowley had hung up on him while he answered, until laughter slowly began pouring in through the phone, the hunter rolling his eyes to the sky as it went on for almost a solid minute. 

 

“Oh my, that was a treat I was  _ not  _ expecting this evening. Forget the sex, all debts are repayed after that one, Squirrel. There are tears, I wasn’t even sure I could still  _ make  _ those.” Crowley said, almost wheezing as he wiped his eyes and tried to regain his composure. “Dean, there are several known laws of the universe which are irrefutable. Gravity increases with mass, black will always be in fashion, and Castiel has an undying love for Dean Winchester.”

 

“Would you stop? That’s not funny.” Dean protested as Crowley let off another bout of laughter. The memory of Balthazar’s jibe of ‘the one with a dirty trench coat, who’s in love with you.’ played itself over in his mind. “Seriously, Crowley, those jokes are getting old. Cas is like my brother, he’s family.”

 

“Oh? Is that right? Well, then, Squirrel, how about a little wager, involving your family? We’ll make it a three parter, over three months time, just for kicks. Say you find out Castiel likes guys as well as girls...you tell him you’ve enjoyed the occasional man in your life recently, and how much fun choking on a fat dick can be. Nothing serious, just some banter between brothers, right? You don’t even have to mention me.” Crowley said, making Dean stop in place and purse his lips together.

 

“If he tells you he’s interested in you, romantically or sexually, well, you tell him I got there first, and inform him of our fun little situation. Details included. After all, just because he’s interested, doesn’t mean you are. And it’s best to let him down easy, let him know there’s someone else giving it to you already. It’s only fair.” he continued, Dean’s blood pumping faster through his veins as his annoyance rose.

 

“And if what I think will end up happening, happens, which is he finally snaps and gets physical with you, then you have to tell your entire family about you and me. Be it a kiss, some delightful dry humping, or maybe he just slides it right inside...either way, no more secrets.” Crowley finished, delighted to hear the other man’s slightly elevated breathing. It was too easy to get on the Winchester’s nerves sometimes. "After you finish banging the angel, of course. No amount of convincing on your part will be enough to make me believe you wouldn't like that celestial's tongue down your throat." 

 

“What about if I win, huh? What happens then?” Dean asked through gritted teeth. Crowley mulled it over in his head for a moment as Dean stewed, knowing none of those things had a chance in hell of happening and wondering what he’d get out of all of this.

 

“Well, the same thing as I would. No more secrets. I tell you about all the little plans I’ve got going on, why I bothered to get Bobby out of that heavenly cage...everything. No more secrets. I’ll even enforce my end with a contract, and let you shadow me for a bit in hell, if you’d like. I know how badly you must miss it.” Crowley said, practically hearing Dean’s gears turning in his head. The king of hell, bound to tell him all his secrets? It was any hunter’s dream.

 

“Deal. But you’re gonna eat your words, Crowley. I guarantee it.” Dean said gruffly, before hanging up and tossing his phone on the bed, joining it a little while later to sleep fitfully and dream of both Crowley and Castiel in various anger, shame, and lust filled visions. 

 

Meanwhile, Castiel stood outside of Dean’s door, his angelic hearing allowing him to have heard every bit of the phone conversation on both ends. For some reason, Dean just couldn’t understand that he lived with someone who could hear from one end of the Bunker to the other very easily with the slightest effort. He looked down at his phone, the text from Crowley he’d received ten minutes prior still open, telling him to go listen at Dean’s door.

 

Down in Hell, Crowley smiled.


	8. Thank Humanity for the Internet

**Summary for the Chapter:**

> Castiel confronts Crowley, and the Winchester Clan starts working out.

Castiel’s hearing allowed him to tell the moment Dean woke up from his restless sleep. He could hear him toss and turn before leaving bed, use the toilet, shower, dress, and eventually go to join Sam and Bobby for breakfast in the kitchen. It was also what had allowed him to hear that Dean Winchester, the man he had been in love with for almost a decade, was sleeping with a demon. A male demon. And not Castiel, the angel who had been by his side, ready to do whatever the hunter wished until the end of time. He was a tad conflicted over this.

 

On the one hand, this was Crowley. A slimy businessman at the best of times, one who would sell his own mother (not unjustly) to serve his own ends if the situation required it. He knew Dean had been very upset to find Sam in some kind of relationship with Ruby, and now the Righteous Man had gone and done the very same thing. Why hadn’t he come to Castiel if he really wanted to sleep with a man? The angel would have been all too happy to be physically intimate with Dean. There was a reason Heaven and Hell both made those jibes, Castiel wasn’t as subtle as he would like to be, but apparently still too subtle for the Winchester.

 

On the other hand, Dean had finally slept with a man, something Castiel was sure he’d been wanting to do for a long while. And he knew Dean had a special connection with the demon, even if he didn’t like it much. If Dean was happy, then who was he to complain? And the thought of Crowley with Dean wasn’t...terribly unpleasant. He knew the demon had an allure to him, a confidence and bearing that had given him a certain ‘sex appeal’. And yet Crowley had made sure he had overheard the conversation last night. Why? To gloat? To inform? Castiel grabbed his phone and stared at it for a moment, before finally giving in and calling the king of hell.

 

“Dean Winchester’s booty-call, how may I help you?” Crowley answered cheerfully in the most singsongy of voices. Castiel shut his eyes and silently begged for strength from above, even if no one was listening.

 

“Explain, Crowley. I trust you know I don’t need my wings in order to hunt you down.” Castiel growled, further annoyed by the chuckle on the other end of the phone. Realistically, were he ever to try to actually hunt down the demon, he had a feeling he would be overwhelmed by hell’s numbers, but he had done the impossible before. “Why tell me anything? Especially if this is supposed to be a secret.”

 

“Technically, I didn’t tell you a thing. I just told you where to be to find out things on your own. Regardless, I’m quite tired of all of Dean’s hiding and denial; all that macho posing is hindering him from reaching his full and slutty potential.” Crowley said, Castiel frowning and wondering how that made sense, given Dean was already sleeping with the demon. Crowley seemed to sense his confusion.

 

“To put it more simply, I don’t want anything holding Dean back from embracing his love of men. His guilt and shame are almost palpable, and, quite frankly, it’s nauseating. He’s worried his family will judge him; I believe they’ll welcome him with open arms. He’s worried you won’t look at him the same way; I’m counting on that, especially since I’m quite sure you both feel the same way about one another. I know that whatever Dean feels for me pales in comparison to the ‘profound bond’ that you both share, but I don’t see why we can’t both have our fun with him, do you?”

 

Castiel thought hard about what Crowley was saying. Both of them with Dean, physically at least. Monogamy was more of a human concept, he didn’t really mind the idea of sharing as long as Dean was happy with it. And while he was sure Dean had feelings for him, as he had been for many years, he also wanted to make sure it was the hunter’s choice. He never wanted the other man to feel forced into anything, or to be ashamed. Lessening Dean’s guilt over any of this didn’t sound like such a bad idea...maybe it would make him more receptive to things.

 

“And how exactly does me knowing about this, and about your ridiculous bet, help with anything? Other than making him angry with you.” Castiel asked, unsure of what Crowley expected from him. Things weren’t usually very straightforward with Crowley, and he didn’t want to make assumptions. 

 

“Feathers, do try to keep up. Think. This gives you the perfect chance at Dean, both to get him in bed and to get him back for all the waiting he’s made you do. He’ll be keeping his eyes wide for any possible indication you might like him. Or men in general, really. The opportunities to mess with him will be...plentiful.” Crowley said, and Castiel’s mind whirled with the possibilities. True, he didn’t really like the idea of ‘getting back’ at Dean, exactly, but the hunter  _ had  _ kept him waiting for a long time...

 

“But I still don’t get what you get out of this. You...you have him, Crowley.” Castiel said, almost defeated. He sighed tiredly, wiping his hand down his face in the way he had learned from Dean long ago. So many human mannerisms from the man he loved. “Even if he does have feelings for me like I think he does, you...won. He’s sleeping with you, and enjoying it, I’m sure.”

 

There was silence for a short while on the other end of the phone. It felt weighted, and Castiel wasn’t sure he could recall a time that Crowley was at a loss for words. Especially when given such a good opportunity to gloat. A sigh matching his own was finally heard.

 

“Truth be told, Castiel...I’ve changed, some, these past months. Or maybe I’ve been this was for a lot longer and just couldn’t admit it. I’ll stab you with your own angel blade if you tell anyone this, but...I want Dean, and the people he cares about, to be happy. Not from some lovesick puppy perspective, like yours. But after after everything all of us have gone through together, I can’t find it in myself to get any of that old hatred for the Winchesters and their lot going again. Now it seems, to quote Hannah Montana, I want the ‘best of both worlds’.” Crowley said, and Castiel was shamed and saddened that the media knowledge given to him let him understand the reference. 

 

“What worlds do you mean?” Castiel said, confused. Crowley chuckled and could be heard sipping on a drink for a moment.

 

“Earth and Hell, my dear angel. I want to rule hell, while keeping you lot as friends and allies...and lovers. Assuming you and I could ever be friends to begin with. I know it’s presumptuous, but I think I can walk what is sure to be a very fine line, and keep access to Dean’s very fine ass. Not exclusively, of course.” Crowley said, and Castiel took a moment to process. 

 

“It won’t be easy, Crowley. You’ve seen how my efforts to be an ally to both Heaven and the Winchesters have gone. Hell may turn on you, if they think you aren’t fit to rule.” Castiel said, surprised to find himself troubled at the idea of the king of hell being deposed, or worse. “And Sam and Dean may not be able to justify you as an ally if you send demons after innocent people on a daily basis.”

 

“I’m taking steps to ensure neither party will have any reason to complain. If all works out according to plan, everybody wins. And if not, well, I’ll have been the first to fuck Dean Winchester. Not to rub it in too much, but he has the finest ass I’ve ever had, and you should get inside it before I make sure it’s too gaping and slick for you to use.” Crowley said, Castiel blinking in surprise as the change in conversation, finding his dick rising in interest.

 

“I...while I would enjoy that very much, I’m still not sure what you expect me to do about it. I’ve tried to give Dean hints and clues for years, with nothing to show for it. He can be very obtuse about some things.” Castiel said with some annoyance, looking down at his pants. He knew that phone sex was a thing, but he didn’t think he’d get hard just from hearing Crowley talk about Dean’s ass.

 

“Well here’s your chance to get a little payback. I don’t expect you to actually take the whole three months, but you have it if you need it. Flirt with him, hint at things, do whatever you angels think passes for a bloody courtship. Point is, he’s going to  _ notice  _ now. Maybe even bring Jack into your little plan, lord knows the boy could use some sexual education.” Crowley said, almost offhandedly. 

 

“I thought Jack’s sexual education would be better coming from a human perspective, but you may have a point. Are you...sure about this, Crowley? Sure that this is something Dean will be interested in? There are many humans who don’t like to share; I certainly have enough poorly written  romance novels in my head dealing with jealousy.” Castiel asked, knowing how difficult it was for Dean to admit to liking anything not strictly macho, let alone possibly sleeping with multiple males.

 

“Trust me, Castiel. Sex and debauchery are very much my department. So far as I can tell, the more men who rail Dean’s holes, the happier he’ll be. He just needs a little help realizing that first. The ball’s in your court now, he’s got his eye on you. Make sure he likes what he sees.” Crowley said, hanging up before Castiel could respond. The angel stared down at the phone, then at the bulge in his pants, wondering if he’d actually get to actually put it to good use. 

 

Castiel thought for a little while, hearing the Winchesters and Bobby talking and laughing in the kitchen. His priorities were to keep Dean and the rest of his family whole and happy, nothing that would cause Dean to shy away from him or distance himself as he had done in the past. Dean was a complicated man, and just because he’d done things with Crowley, didn’t mean he was suddenly going to be open and willing to do anything and everything. He needed to plan.

 

Lying back on his bed, Castiel got his laptop (really the only thing besides reading that he used his bed for) and opened it up, staring at the search bar for a moment before beginning to type. He had been a commander when he was properly part of heaven, and as every leader knows, you need information before you make a move.

 

_ Thank humanity for the internet. _

  
  


________________________________________________________________________

  
  
  


“What do you mean you can’t find something? There’s no hauntings in Arkansas, no werewolf in South Dakota? Not anything?” Dean asked, looking over Sam’s shoulder at his computer and hoping he could see something he brother couldn’t. Sam gave him an annoyed look and scrolled so Dean could see that, in fact, he wasn’t crazy.

 

“Yeah, it’s weird. I’ve gotten a few police reports here and there that looked like they could have been something, but every time I’ve sent a hunter to go check it out...nothing. I haven’t been checking in as much since Bobby got back, but I called around to some of our guys and they all say the same thing.” Sam said, frowning at his computer as he double checked things yet again. Every time he thought he had found something, it turned out to be a stray dog or a prank by kids. No actual monsters.

 

“What is it, some kind of monster holiday? I mean, I’m not gonna complain about some more down time, but I haven’t stabbed anything in a while. Feels unnatural.” Dean said, trying to think back to the last time he’d been on an actual hunt. With all the stuff with Michael and Jack going on, and his previously injured state, he hadn’t gotten any good old fashioned ganking in. And Crowley hadn’t contacted him in almost a week, which was weird...and it was still hard for Dean to make the first move. 

 

Mary and Bobby had left yesterday to check out Bobby’s old home, or what was left of it. They were going to see about any legal stuff they needed to take care of, and if Bobby was interested in rebuilding. They had a new (to them) and awesome bunker, but that didn’t mean the man wouldn’t want his old home back. The place was a little quieter with them gone.

 

“Yeah. I’m gonna check in again in an hour or so when we get back.” Sam said, shaking his head and shutting down his computer. Dean frowned and followed  as his brother walked towards the kitchen, not remembering if they had anything planned.

 

“Back? From what, a beer run?” Dean asked as they walked into the kitchen, freezing in place as the image before him came into view. He almost didn’t recognize the person drinking from a water bottle at the table. Castiel had his back turned towards the both of them, dressed in a tight grey t-shirt and black running shorts. “Woah.”

 

“I’ve been working on getting Jack to go jogging with me lately, and when Cas said he would join us, Jack finally agreed. I’m gonna go wake up Jack and get changed, meet you outside in ten?” Sam asked Cas, who nodded as he finished drinking and screwed the cap on before turning to Dean.

 

“Good morning, Dean. I asked Sam if we should invite you, but he told me you ‘hate jogging with a passion only trumped by spewing witches’. What brings you up this early?” Castiel asked casually, inwardly hoping he looked appealing. He watched Dean’s eyes take in his appearance, heard his heart rate increase and saw a little blood rush to his face. Being an angel had its perks sometimes.

 

“Sam was just...uuuh...just showing me something. Why um, why the gettup? I didn’t think angels needed to exercise.” Dean asked, working hard to keep his eyes on Cas’s face. The shirt was very tight on him, and it always shocked and aroused Dean when he remembered just how muscular and toned Cas was underneath his usual layered outfit. Dean still had his robe on, and despite its comfort, he knew he probably looked kind of frumpy. 

 

“Well, in all our research on trying to help Jack, I realized something. Angels not only become more like humans when they lose their grace, but they can  _ choose  _ to become so, and enjoy what parts of humanity they desire. It’s how Gabriel was able to enjoy eating and other human activities so much, despite angels not normally being able to taste.” Castiel said, picking up a plate with crumbs on it and showing it to Dean, getting a little closer in the process.

 

“I’m working on getting my taste buds to cooperate, and jogging seemed like another way to feel more physical human aspects, like being out of breath, sweating. Feeling my body.” Castiel said, keeping his voice casual. He could see Dean’s eyes react, and he knew he was doing well. He was grateful and surprised it seemed so easy to get a reaction. Maybe he wouldn’t have to wait long for Dean to snap.

 

“Well, that’s...that’s great, Cas. Humanity can be kinda fun sometimes, I guess. When you get your taste buds workin’ right, let me know, I’ll cook you up a mean burger.” Dean promised, smiling as he eyes darting ever so briefly to Castiel’s mouth. The angel smiled, almost a smirk, and nodded slowly.

 

“I’d like to taste it again...your cooking. I didn’t get to enjoy it much when I was human.” Castiel said, and Dean’s eyes widened a bit as he got closer...but all he did was reach behind Dean to throw the plate away. “I believe the others are ready, are you sure you don’t wish to join us?”

 

“I, uh...don’t think I’d fit into shorts that tight, man.” Dean said, making the mistake of looking down at Cas’s shorts and seeing the slight bulge there, his face going redder as he made an escape into the fridge to get something for breakfast. “But you guys have fun, I’ll just chow down and get fat.”

 

“You’re not fat, Dean. You have a good metabolism, and hunting keeps you quite fit. But Sam is right, your diet...could use a little altering, if you’re worried about getting out of shape.” Castiel said, using the opportunity to look Dean up and down as if he was looking at a science project. In reality, he wanted to climb into the hunter’s robe with him and hold him close, but that would need to wait. Dean looked a little uncomfortable with the angel’s gaze on him as he set the milk out on the counter and hesitated as he went to grab a very sugary cereal.

 

“Cas? Sam’s outside, are you coming?” Jack said from the kitchen doorway, both other men looking up at him. He had a similar shirt on as Castiel’s, but white, and his shorts looked similar too. Probably all bought at the same place, Dean thought, as he waved to the two fitness gurus while they walked out. Jack looked like he didn’t really need to jog either, trim muscle showing easily on his young frame. 

 

Dean was torn between feeling old, left out, out of shape, jealous...and aroused. Who the hell thought it was legal for that angel to be walking around in one, very tight layer instead of his usual trench coat? Ever since Crowley had brought all this to the surface, he had a harder time not noticing when guys looked good, especially his roommates. 

 

Dean looked in the cabinet they kept the cereal for a few moments, deliberating, before he pulled out the healthier brand that Sam used and made himself a bowl. He hated every second of it, but he chowed down on it as he thought. After he put his bowl in the sink, he went down a hallway near the bedrooms that they didn’t often go down. Group showers were here, which they mainly used to clean up after particularly gross hunts, and a small gym area with weights and other dated equipment. He looked around for a bit before picking up a couple of weights.

 

“Well...no time like the present.” Dean said, shedding his robe and taking a deep breath, resolving to clean up the room and make it more presentable later on. For now, he looked at himself in the mirror, and started to pump some iron. No way Dean Winchester was getting flabby while the rest of his family turned into fitness freaks. He’d show them that jogging wasn’t all it’s cracked up to be.

 

**Notes for the Chapter:**

> I want people's opinions: Should I post a chapter listing all the physical stats, sexual preferences, and even stuff like dick sizes as a chapter? Or would that ruin people's immersion? I don't want to give too many spoilers, but there's going to be people coming back to life (I know, such a weird concept with this show) and I don't have to if it's not wanted.


	9. Showering Sensations

**Summary for the Chapter:**

> Castiel finally unlocks his humanity, with perfect timing...

“Well?”

 

“...passable, for beginners.”

 

“High praise if I’ve ever heard it, coming from you.”

 

“Now don’t get your gold stars out just yet, princess. They got a long way to go, and they’re still way too focused on using their demon mojo to solve problems.”

 

“But that’s why you’re here, Bobby. And doing a splendid job so far. Now, given their progress, how does going back upstairs early sound?”

 

“...no strings? This is still their first week.”

 

“Well, unless you  _ want  _ to give me a smooch of appreciation...” 

 

“Pass, but good to know I ain’t stuck down here. Same time next week?”

 

“They’ll have gone through all the drills you’ve left them, or their flesh will be used to feed the hounds.”

 

“Whatever keeps them practicing.”

 

And with that, Bobby Singer’s soul resumed it’s bright blue glow, and he ascended through Hell’s many levels quickly, past Earth, and into Heaven with his wife and son. Crowley watched it rise with some fondness, having grown to appreciate this version of the hunter almost as much as the other one. Still no kiss though, and after this long without Dean, Crowley could feel himself getting antsy for some action.

 

Not that he didn’t have any other options...he looked over at Antonio, training some of the demons that were having a harder time adjusting to all the new ways of fighting. Him and the other demon certainly were able to help each other release some steam...and goodness knows what a fine body and equipment he possessed, but it still wasn’t quite as satisfying as making a whore out of the Winchester. Still, Crowley was patient, and a grateful and accepting Dean was something worth waiting for.

 

Now if only that damn angel would hurry his fine ass up...

 

______________________________________________________________________________

  
  
  


“Still trying to wrap my head around the angel stuff. So, you really couldn’t sweat before? Or even get tired?” Mary asked, looking bemused at a panting Castiel in the bunker’s kitchen. Sam and Jack both looked equally winded, but they had humanity to blame, and Sam had a huge grin on his face between taking long drinks of water. 

 

“He finally figured it out when we were halfway back from our run. We could barely keep up with him, he was so excited about it. He kept going on about skin temperature and having to breathe differently.” Sam explained as Cas just smiled with his hands on his knees, rising up and putting them behind his head.

 

“It’s just so wonderfully complicated. Technically it’s a negative experience for the body, something that’s used when you have to chase or flee, but it feels so...refreshing, and exhilarating at the same time. Even when I’m tired from fighting something as strong as I am, it’s not the same, not the same rush.” Castiel explained, just enjoying the feeling for a moment while Jack started looking around the fridge. 

 

“Well, I’m happy for you, and glad you all decided to take this up while we were gone. God knows we’re having a hard time finding anything to hunt or do with our time. Bobby’s going through some old contacts and seeing if we can figure out exactly what’s causing all the monsters to disappear, or go into hiding, or whatever it is they’re doing. I’m going to go do the same, if anyone wants to join me.” Mary offered, Sam nodding while he finished his water and Jack poking his head out of the fridge.

 

“I’ll go too; jogging has been the only thing that’s gotten me out of the bunker recently. Could we stop for something to eat? Maybe some barbecue?” Jack asked, Mary smiling fondly and nodding as she walked with him out of the kitchen. Sam refilled his water bottle and looked over his shoulder at Cas.

 

“What about you? Feel like taking a trip?” Sam asked, and Castiel looked at the younger Winchester for a moment, admiring his tall and muscled form. He kept himself in better shape than his brother, in many ways, but while Castiel knew Sam was very attractive, he was fascinated by the difference in his feelings towards the two brothers. Speaking of Dean...

 

“No, you three go, I’m going to keep experimenting with this...newfound humanity. I’ll let Dean know about your excursion, I can hear the shower going.” Castiel offered, Sam nodding and heading towards his room to shower and get ready. The angel waited till every human was out of hearing range before running towards the bathroom Dean was in, which was not the one closest to his bedroom, he realized. He was in the group showers, further away from everyone else, which would suit his plans quite well. 

 

The entire week since their exercising started, Castiel had been memorizing what time Dean’s alarm had been going off each morning, and it was definitely earlier than it used to. Most of the time, he was there in the kitchen waiting for them when they all got back from their run, eating breakfast and poking fun at them for how tired and haggard they looked. But Castiel saw where the hunter’s eyes rested most of the time...him. And because of his rush to get back, they had returned before Dean had even finished showering. The angel ran a few times across the hall in front of the bathroom door, just to get his breathing and heart rate up, when the shower stopped. Castiel waiting a couple moments, silently stretching and feeling his body, before knocking. 

 

“Yeah?”

 

“It’s me, Dean.” Cas said, breathing hard and loving how his voice sounded when he was winded. He hoped Dean liked it, hoped he would get to get winded with Dean quite often, in ways not involving jogging. He heard the towel get quickly used on the hunter’s hair, and he swore he could hear Dean attempting to style his hair a bit before wrapping the towel around himself and opening the door.

 

As much as both men wanted to act normal, neither had the capability for a moment. There Dean was, water droplets running down his beautiful torso, steam billowing out around him. Castiel wanted to feel his skin and force him back in the shower, just to make sure he had really scrubbed himself everywhere. Dean’s arms and chest looked suspiciously more defined than in weeks previous, and Cas started to put together a few more pieces of exactly what Dean was doing while they ran.

 

Cas was just...he looked filthy, in the best damn way possible. Sweat had soaked through a lot of his grey shirt, making it cling to his body in a way that was almost obscene. His hair was a disaster in a way that made Dean want to grab a fistfull of it and...god, the angel was just breathing hard and  _ staring  _ at him. He felt his cock start to grow in interest, so he cleared his throat and quickly swallowed.

 

“The hell happened to you? You get sucked into a tornado?” Dean asked gruffly, like he was being inconvenienced instead of being given a treat, using the opportunity to look Cas up and down without the question of him being a pervert coming up. He tried to keep his heartbeat from going insane, but he hadn’t been prepared to find this outside the door. Castiel just grinned at him, blinding and beautiful and...yeah, there went his heartbeat.

 

“I did it, Dean, I figured out how to tap into my vessel’s humanity. I can feel everything: my heart racing, my lungs working to give me oxygen, how crisp the air is, what a relief a glass of water is...I can even feel the humidity coming from there.” Castiel told him, raising a hand and waving it towards the bathroom before finding himself staring at one of the many showers the room held, a brilliant idea popping into his head. Quick as a flash, the angel pulled off his shirt, walking towards Dean, who backed up like the angel was brandishing a hot poker at him.

 

“Cas??” Dean asked, his eyes wide and cock stiffening as he got a huge eyeful of tanned flesh and muscle before it stepped past him towards the shower, Cas reaching inside and turning on the water. He tried and failed to pull his eyes away from the gorgeous sight of Castiel’s toned back and barely covered ass as the angel let out, god help him, a moan as his fingers came in contact with the hot water.

 

“I haven’t been able to enjoy a hot shower in so long, angels don’t-” Castiel started, cutting himself off and looking sheepishly over at Dean with an apologetic look on his face. “I’m incredibly sorry, Dean, that was rude of me. Are you done with the shower?” he asked innocently. In reality, he knew exactly what he was doing to Dean. He could see his poorly hidden erection without looking down, could hear his erratic heartbeat and his shaky breath.

 

“I...yeah, man, have at it.” Dean said, just watching as Cas knelt down and started to remove his shoes. He tried to find any excuse to stay as the angel’s footwear was removed, but he knew he was sporting some hard to hide wood, so he grabbed his clothes and turned to leave so he could run back to his room.

 

“Oh, Dean?” Castiel said, removing the final sock and standing up as the hunter turned back towards him, poorly covering his bulge with his held clothes. “You mother, brother, and Jack are going to go out to get in contact with some other hunters, if you felt like joining them.” he continued, before shamelessly pulling down his running shorts and underwear in one go, his eyes taking in the Dean’s expression.

 

Dean couldn’t have kept his eyes from the sight if he had wanted to, Cas’s semi-hard and impressive looking cock waving as he turned and stepped into the shower. The angel closed his eyes and let out a loud sigh of pleasure as the hot water started running down his body, Dean rooted to the spot with his mouth parted slightly. 

 

_ Leave, leave right now. He just doesn’t get social cues, he showed up naked on your car and covered in bees once. Stop staring, stop staring, he’s your  _ friend _ , he’s an  _ angel _ , stop _ . Dean thought wildly as his eyes roamed over Castiel, Angel of the Lord, who had the most sinful body he had ever seen. All trim muscle and beautiful skin and...Cas leaned back to wet his hair, moaning quietly as he ran his fingers through it, and Dean’s entire body  _ pulsed _ . The angel opened his eyes and looked right at Dean, his expression unreadable.

 

“Was there anything you  _ needed  _ from in here, Dean?” Cas asked, his voice...Dean couldn’t tell if he was asking him anything, if he was insinuating anything, but he knew that it wouldn’t matter, because he would be back in that shower in about five seconds if he stayed.

 

“Enjoy your shower.” Dean said quickly before closing the door behind him, staring down at the handle, unable to let go. That is, until he heard another little sound of pleasure from Cas, and he booked it down the hallway to his room before he decided to barge back inside. He begged every deity he had ever heard of to not let any of his family see him walking around with the biggest boner he’d ever had.

 

Castiel really was enjoying the water, to be fair; not all of it was just a show for Dean. With human sensations available to him, everything felt more intense and amazing. The water was almost too hot, and he relished the feeling of it pouring over his skin. He grinned as he felt the cold come into the shower, and looked around briefly before he closed the curtain. The room was similar to a gym locker room, with a dozen showers each separated by tiled dividers, and benches in the area between for people’s clothes. 

 

The angel kept his ear out for what Dean did, hearing him shut himself in his room and lock the door, his breathing labored. Castiel gently felt himself up and down, feeling the wonderful sensations on his skin, and wondered how far he should take this. His questions were answered by a muttered ‘damn it’ from Dean, who proceeded to lie down on his bed and started to feel himself in an even more perverted way than Cas was doing.

 

“Dean...” Castiel breathed out, his cock rising to full attention when he realized Dean was stroking himself. He focused more intently, hearing the hunter’s breath pick up, hearing the slide of his hand against his cock and he gripped and squeezed. This was interrupted as Sam knocked on his brother’s door.

 

“Dean? I know you’re getting dressed, did Cas let you know about the three of us going out? You gonna join us? Mom and Jack are both in the car, but we could wait for you if you’re coming.” Sam said, Dean letting out a whispered curse. Castiel smiled, looking down at his own cock standing at attention, knowing how frustrated Dean must be. He couldn’t lie, it was nice that Dean was getting a little taste of what Castiel had been going through for nearly a decade.

 

“Nah, I’ll start searching here on my end in a bit, you all enjoy yourselves!” Dean insisted, maybe a little too enthusiastically. Both naked men could practically see Sam’s concerned frown without actually seeing his face, but Sam just knocked twice to acknowledge his brother and walked away towards the garage. Dean gave it about a full minute before he started pumping his cock again, giving out a little moan.

 

Castiel joined the hunter slowly, having only touched himself a few times in his existence, but he let out a surprised groan when he realized the sensations were even better than they normally were. As part of his research, Castiel had watched quite a bit of gay porn so he would know what to do if Dean ended up agreeing to sleep with him, so he knew how to work his hard shaft and pleasure himself. He also knew that he was a little over seven inches long, quite thick, and that his genitals compared well with many of the men he had seen online. 

 

“Dean, I can’t wait to do this with you...” Castiel admitted quietly, leaning back against the cold wall and sliding his hand along his rod over and over again, his head falling back and his mouth opening as he heard Dean’s strokes begin to make wet noises from all the precum he was producing. Every sound the hunter made went straight to the angel’s cock, and both men were having a hard time controlling themselves, urged on by the fact that they were the only ones in the bunker. 

 

Dean’s breathing was getting rougher, his moans coming more frequently, and Castiel knew what that meant. He couldn’t stop the gasp when Dean said his name once, then twice, clearly imagining Cas in the room and doing things with him. The longing that the angel always felt from the human was stronger than ever before, and driving him crazy with want, forcing him to stroke harder and faster as Dean did the same.

 

Normally, Castiel was able to control his erections and ejaculations much more easily with his grace, but as Dean reached the edge, so did Cas. When Dean started to cry out, Castiel let out a shout of surprise, followed by several others, as his orgasm was almost punched out of him by every sound his ears were hearing. Cum rocketed out from his dick, paining the curtain in front of him in white as the angel kept squirting more and more spunk out of his slit. Dean was done within a minute, but Cas had to squeeze his eyes shut and keep pumping out far more than any human could produce, finally sagging against the wall as his orgasm ended nearly two minutes after Dean’s. The angel could hear the hunter’s ragged breathing and satisfied sighs, and smiled.

 

“We are definitely going to have sex in the shower. And everywhere else.” Castiel promised the man who couldn’t hear him, cleaning the curtain with a wave of his hand as a lazy smile crossed his face. His heartbeat was starting to slow down, his breathing evening out, and his whole being felt more alive than he could ever remember. Oh yes, he thought as he relaxed under the hot water, this was going to be so much fun...

 


	10. Angelic Lessons

**Summary for the Chapter:**

> Castiel helps teach Jack about sex in a purely scholarly manner....at first.

  
“We found him attempting to find a way to communicate with Lucifer, my lord, asking around some of his few remaining old loyalists. He and the demons he summoned are in custody, save for the one who turned them in.” Antonio reported, indicating a stunning brunette demon next to him with a nod. Crowley looked her up and down, before eventually placing her.

“Bela Talbot, if I’m not mistaken. One of our rising stars, if the scores from our new little tests are to be believed. Previous dealings and bestings of the Winchesters, and many victories of your own besides. Tell me, why did you turn them in? Surely the possibility of helping to resurrect Lucifer and be in his good graces was a tempting proposition.” Crowley asked from his throne, looking her up and down again. He remembered approving her request to have her own human corpse restored so she could use it as a crossroad’s demon, and her ability to close a deal was such that Crowley had no issue with the request. 

“I thought about it, my lord, but I wasn’t convinced. Lucifer has failed to achieve any of his goals, whatever they actually are, at every turn. I didn’t trust that his discarded meat suit would have any luck getting him back, and even if he did, that Lucifer wouldn’t end up dead or captured again. After all, he’s gone, and you’re...well, sitting on the throne of hell. I’d rather put myself in your good graces.” the demoness replied charmingly, with a million dollar smile. Crowley smirked, seeing through the flattery, but it was just so well executed. 

“My dear, you have done so, beautifully. In my new blueprint for hell, intelligence and common sense are qualities I value highly. Antonio, put her through the next stage of trials. We’ll see if you have what it takes for some of the newer topside missions. I trust you’re no stranger to combat?” Crowley asked, figuring if she’d dealt with the Winchesters, violence was probably involved.

“Of course, my lord. Thank you, you will not be disappointed.” Bela said, a hint of desperation breaking through. It wasn’t that long ago she had been on the rack, but the nature of her contract and her history as an expert of supernatural goods had given her an ‘early release’ of sorts, and she was determined not to ever go back. She was lead out by a couple other demons, Crowley stopping Antonio on the way out and whispering to him.

“Keep a close eye on her; if memory serves she’s a conniving one, and I wouldn’t put it past her to attempt an escape, or even succeed. I’m going to go pay our new guest a visit, and take care of his little helpers, but I trust I’ll see you later in my chambers. On your knees, naturally.” Crowley said, giving the other demon a bit of whiplash with his change in topics, before he nodded and smiled. The king of hell straightened his tie and began to walk to the prison cells.

It was time to see what the little vessel he’d restored so long ago was up to...

  
______________________________________________________________________________

 

This was less fun than Castiel had first anticipated. When he had displayed himself so brazenly to Dean, he had assumed the other’s very positive bodily reaction would mean he’d be eager to see Castiel in similar states of undress more frequently. Instead, it seemed that Dean could barely look at him. Dean was hardly ever in the kitchen when they returned, and when he was, he had a hard time looking at the angel. Instead Castiel could hear him working out in the bunker’s small, antiquated gym...which did admittedly have a good effect on Dean’s muscles, but was still frustrating. 

It was this frustration, as well as the sound of Dean in the shower, that was distracting Castiel from what Jack was attempting to show him. The two of them were in Jack’s room, sitting across from one another on the Nephilim’s bed. 

“I think I did it, I can’t feel any more damage...Castiel? Did I do something wrong?” Jack asked, slowly lowering the potted plant he had repaired the broken branch of. Castiel was trying to work him up to healing people, but felt it prudent to start with other, less sentient forms of life first. The angel shook himself a little, smiling and examining the small fern.

“No, you did perfectly. Tomorrow we can go out and find some injured animals to help, maybe stop by a vet’s office. Unless we can figure out where all these monsters keep disappearing to. Sam seems like he’s ready to pull his hair out.” Castiel said, feeling sorry for the younger Winchester as he placed the fern on Jack’s bedside table. The longer they went without work, the more determined Sam seemed to find out what had happened. 

“I know. He’s even stopped giving me homework, but he said I was close to learning everything he could teach me anyway. Well...almost everything.” Jack said, looking down at his hands as he thought about what he had asked Dean not too long ago. Castiel frowned.

“We’re working on your powers almost daily, Jack, and you’ve gotten far better at controlling them. And so far as I know, Sam is a very good teacher of all things human, especially with everyone else supplementing in their own ways. Was there something else you wanted to learn about?” the angel asked, wondering what wasn’t being covered. 

“I had asked Dean to, well, teach me about sex, and he said he would talk to you about it, but I don’t think he ever did. He wanted to see if there was anything angelic to worry about that would be different for me. I don’t blame him, with Bobby coming back and all of these monster mysteries, I understand he’s distracted. But I’m just so...frustrated.” Jack admitted, looking down in what Castiel first thought was shame, but then realized that Jack was looking down at the tent in his pants. Just talking about it had gotten him hard, and Castiel immediately sympathized. 

“Oh, Jack, I thought one of them might be a better teacher on the subject because I’ve done so little in the way of sex. Not for lack of desire, just...with the way our lives are, I don’t think even Sam and Dean have had much time for copulation. But I can try to tell you what I know.” Castiel said, Jack grinning up at him in response and making the angel’s heart warm. He got up to retrieve the Nephilim’s laptop, locking the door behind them for privacy before sitting back on the bed, this time the two of them sitting with their shoulders touching at the head of the bed.

“Now, in purely biological terms, sex is primarily meant for procreation, so we’ll start with that.” Castiel said, bringing up an article he’d read when he was first learning about sex, and began to show Jack a few very technical diagrams, explaining what the purpose and function of everything was. But Jack stopped him after only a few moments.

“Oh, I...sort of read most of this already. I went looking when it seemed like Dean had forgotten to talk to you, and I found a lot of this stuff talking about how sex technically works, but Sam’s ‘internet protection’ stuff doesn’t let me go to some of the sites for some reason.” Jack explained, and Castiel’s eyebrows rose. He hadn’t realized that Sam had blocked porn on Jack’s computer, but he supposed he could understand the caution. 

“So if you’re aware of how it works, what questions do you have?” Castiel asked, noticing the young man shifting and the large bulge that moved in his pants. He was wearing black sweatpants, and they did very little to hide the fact that Jack must be quite large. It was giving the angel a little hard on of his own, but he ignored it and focused on Jack. 

“Well, I guess like how you train me to fight? I could read books about fighting all day long, but it wouldn’t help if I didn’t actually do it. I don’t know how to find someone who would want to do it, or what steps to do first, or what to do after...the only people I’ve ever wanted to do it with are you and Dean, so I don’t know if I should go and meet more people.” Jack said, palming his erection like he was trying to make it go away, but it just seemed harder when he stopped. 

Castiel thought about all of that in silence for a moment. There were things he was less sure of, like Jack was, like the best ways to initiate those kinds of situations. It seemed so easy for Dean, and even Sam. His first and only had been a fluke, and the reaper had killed him afterwards, so it wasn’t much of a good example. But Jack being attracted to him and Dean...that was something he wasn’t expecting.

“So, so far, the only people who have caused...that, are Dean and myself?” Castiel asked, pointing to the Nephilim’s erection, to which Jack nodded. “Well, angels don’t have the same problems that humans seem to when it comes to sleeping with their brothers and sisters, so I have no issue with you being attracted to me, but...they are correct about beings waiting until they’re mentally mature enough for sex.”

“How do I know if I am? I’m a good fighter, and I learn things really quickly. Does that mean I’m mature enough? Or do I need to pass some kind of test?” Jack said, eager now that he was learning things he hadn’t before. Castiel smiled and put a hand on his shoulder. 

“You’re utterly unique, Jack, more than most people. But the rule for human adults to have sex with one another in this country is, for the most part, both members must be 18 years of age. Given your rapid aging into a young adult, it’s hard to say when that ‘mental maturity’ would be for you, but...if you’d allow it, I can attempt a sort of ‘test’, if you’d like.” Castiel offered, the Nephilim nodding quickly. With that, Castiel closed the laptop and put it away, then placed his fingertips gently on both sides of Jack’s temple and closed his eyes.

Castiel knew there was little he could do to hurt Jack, but he was still careful as he gently examined the mind of his young charge. He didn’t sift through memories so much as the impressions he got, the changes Jack had gone through. His mind was incredibly sharp and adapting, and though he lacked experience, Castiel could feel the state of his mind and character. With all he had gone through and learned, and with all of them teaching him, Jack had grown into a fine young man. 

“You understand that actions have consequences, that being kind to others is very important to living life. You have respect and compassion...nothing in here gives me reason to believe you aren’t ready for new experiences, such as sex, so long as you’re careful and smart about it.” Castiel said, removing his hands and opening his eyes, Jack grinning in response. 

“Does that mean we can have sex?” Jack said, his eager eyes and closeness surprising the angel, who started to realize just how Jack wanted him to ‘teach’ him. He felt himself harden, but took a breath and turned away, hanging his legs off the bed. He could hear the disappointment in Jack’s voice. “Unless...you don’t want to. I know sex needs both people to want it.” 

“It’s not that I don’t, Jack. Gender makes no difference to me; you’re a very attractive young man, and I love you dearly. But...” Castiel said, debating how much to tell him. The Nephilim joined him on the side of the bed, looking lost, and the angel sighed. “I have feelings for someone else, romantic feelings, and I very much want to have sex with them. I’m open to having sex with multiple partners, since I’ve never fully understood monogamy, but I was hoping to have him be my first, at least when it comes to someone I care about.”

“You’re talking about Dean, aren’t you? I’ve seen the way you both look at each other, but I wasn’t sure if that’s what it was.” Jack said, Castiel looking at him with some surprise, which prompted a shrug. “Sam and Bobby have made some...comments, when you’re not around, about your lack of subtlety.”

“I see. As I’m sure you can tell, Jack, this is new to me too. I’m not experienced like Sam or Dean are in this area. And while I’m quite certain Dean is attracted to men, I’m not sure he’ll ever be able to admit it to himself. He’s rather...stubborn, in that regard. Humanity’s different cultures unfortunately are not always kind to those who are different.” Castiel said, annoyed as his Creator for letting the world become as it was, so full of hate and disharmony. 

“What if I helped?” 

“...what do you mean?”

“What if I helped you and Dean have sex? Then could I have sex with you? And maybe him too?” Jack offered helpfully, like he had just offered to wash the dishes or mow the lawn. Castiel smiled, not disliking the image of the three of them together, and he had to work to repress the urge to touch himself. Jack was different than Dean, less the heavy weight of lust and more the lighter kind of fun for Castiel. 

“I don’t think it’s quite that simple, Jack. I’ve been trying to get Dean to notice me for years now. I even think I’ve succeeded, but just because he’s attracted to me, or even to both of us, doesn’t mean that he’ll be willing to sleep with us. People, humans especially, are complicated.” Castiel informed the younger man, who nodded, thinking for a moment.

“Well, it sounds kinda like the hunt we went on a while ago, that vampire nest in Washington? Dean tried cutting himself a little, then a little more, but it wasn’t till him and Sam both let out a lot of blood before the newborn vampires all ran out into the trap. So...maybe if we both try really hard, he’ll get so frustrated he just...” Jack said, trailing off and palming at himself again, Castiel looking him over when he saw the lust in his eyes appreciatively. 

“He’s not the only one who’s frustrated, is he? I’m sorry this has been so hard on you. I should have tried to help you more in the beginning.” Castiel said apologetically. Jack looked over at him sheepishly, then down at his pants.

“I know you don’t want to have sex with me yet, but could we still do...something? I don’t know, anything. I feel like my body’s on fire.” Jack said in exasperation. Castiel hesitated for only a few seconds before leaning in closer to the Nephilim, using his hand to guide the other man’s lips to his own, giving him a chaste kiss before leaning back a bit to look at Jack’s face. 

“More?” he asked, Jack nodding and giving a little moan as the angel leaned back in. Less chaste this time, lips moving and working together, Jack’s hands coming up to frame his face as Castiel did his, mirroring him as best as he could. Castiel pulled away, breathing heavier, and rock hard in his pants. “Tell me if you want me to stop; kissing is one thing I do have some experience with.”

With that, he plunged back in, Jack letting out desperate, muffled noises when Castiel thrust his tongue inside, the poor Nephilim’s cock throbbing and leaking as the angel began to dominate the kiss, pushing the younger man down and onto the bed. Jack put his arms around Castiel’s neck and whimpered as his legs were pulled apart, the older angel putting himself between them and allowing first contact between their clothed members. Both men pulled their lips apart and gave loud grunts of surprise as pleasure radiated into their whole bodies. They were still and silent a moment, looking into each other’s eyes, before Castiel looked at the door with glowing eyes.

“It’s not perfect soundproofing, but it will do for now. I said I’m not willing to have sex, and I meant it. But if all our clothes stay on, it’s not exactly sex, now is it?” Castiel asked, looking down at a panting Jack with a grin that was almost predatory. “Are you alright with that? Many humans prefer their first times to be more romantic, or eventful, or-” Jack silenced him by pulling him down and closer into a kiss, surprising him with a thrust from below that made the angel groan into the other’s mouth.

Both were sloppy, and both didn’t care. It felt so fucking good just to have contact with someone, to have friction and pressure on their neglected cocks, their mouths messy and desperate. Jack could feel the power and muscle Castiel possessed, tears in his eyes as he finally got what he craved so badly. For all his claim of inexperience, Castiel certainly seemed to know how to do this, and the iron rod Jack could feel grinding against his own let him know the older man was loving this too. 

Slowly, Castiel started to thrust against the younger man in earnest, causing cries of pleasure from Jack as he was slowly being brought to where he had never been. Castiel wanted to prolong this, but he knew what Jack really needed, and he covered the Nephilim’s mouth with his hand as he attacked his neck with his mouth and tongue. Soon the young man was screaming and bucking wildly, Castiel smiling as he felt a huge warmth start to expand on his groin as Jack began to pump a huge volume of cum into his sweatpants, every thrust forcing another spurt of cream out of him.

“You’ve certainly got that from your angelic side.” Castiel commented as he looked down between them, Jack still leaking out cum and whining against his fingers nearly three minutes later, his mess too big for his pants to hold. His seed covered his pants, and his shirt and Castiel’s dress shirt was soaked through. Castiel raised himself onto his knees and examined his handiwork. 

“I’m...I’m sorry...that was so, so amazing...and that’s not even the sex part? It gets better?” Jack said, looking like his mind had been blown. Castiel nodded and smiled, looking down at his own erection and wondering what to do about it. This was Jack’s first, and he looked down for the count. 

“Do you want me to show you how to handle this yourself, so you don’t have to wait for me or someone else to help you find relief? I need to ejaculate, to cum, very badly, so it would help me out as well.” Castiel said, his breathing ragged, hardly waiting for Jack to nod as he undid his belt and pulled down his zipper. Still tired, but incredibly interested, Jack sat up as Castiel yanked down his pants and underwear enough to free his rock hard cock.

“Oh wow, that’s...I want to touch you, can I...?” Jack said, Castiel shaking his head no as he slowly began to pump himself, aiming the head right at the Nephilim. Jack had gotten his pleasure, now it was Castiel’s turn to get off, and he’d watched enough porn now to know a good way to finish. Jack’s cum made perfect lube, and the sound of his slick hand sliding over his dick was loud and had Jack’s undivided attention. 

“Not until we see what we can do about Dean. I’m going to let you help, but first I need to finish all over you. See that mess you made? I’m about to do the same thing.” Castiel ‘explained’, loving the look of lust and wonder that came over Jack’s face, making the angel’s cock even harder. He hadn’t understood why all the pornstars came all over their co stars' faces and bodies. Now he knew, and he was about to give Jack one hell of a shower. 

“Here it comes....” Castiel said, his voice low and quiet as white liquid began absolutely pouring out of his cock and all over Jack’s helpless body. He grunted loudly as his orgasm really hit, his cum shooting all over Jack’s surprised face, neck, and chest as Castiel unleashed himself. He claimed Jack, dominating him, covering him with his release and loving every second of it, an exhausted but unmistakable smile on his face by the end of it. “Did you like that, boy?”

Angels came several times as much as humans naturally, and could increase or decrease the amount at will. Castiel had increased his on purpose, and there was hardly a place on Jack or his clothes that hadn’t been hit, looking like a dozen men had had their way with him. The young man looked up at him, a small smile on his face.

“Yes...can you show me again?” Jack asked, his cock already hard again, and Castiel grinned.


	11. Old Home, New Developments

**Summary for the Chapter:**

> Jack's powers continue to develop, as do the relationships of some old friends.

**Notes for the Chapter:**

> I'm so sorry this one took so long. Going through some personal stuff that made inspiration impossible for a while. With the holidays coming up I don't know how often I'll be updating, but I'll do what I can!

Dean had forced Castiel to watch enough cowboy movies that the angel could recognize a standoff in the middle of town when he saw one. Granted, they were in the Bunker, and they were both on laptops in the library, but the feeling was quite similar. Castiel had listened from his room and waited until the hunter had gotten his coffee and sat down to do research, then had promptly joined him without asking. If Dean wanted to ignore him, he would make it just a tad harder for him.

 

“Mornin’. Anything?” Sam asked, walking in with his own laptop, having jogged and showered already, a smoothie in his hand. Why couldn’t have Castiel fallen for the brother that liked to communicate? Dean had barely nodded at him when he sat down.

 

“Nada. If anything, we got less reports than ever. Jack, Mom, and Bobby went to check out a haunting near Sioux Falls, but got bupkis when they showed up. Now they’re heading to Bobby’s old place, see if they can rebuild once Bobby’s got all the legal stuff taken care of.” Dean reported, not looking up from his laptop as he typed away.

 

“Same here. I asked a few hunters to look into something that looked like a Wendigo, but it seems like it was a wild animal. I even asked someone in Heaven if they had any clue what was going on, but their numbers are too few to keep a watchful eye on things. It’s all they can do to keep Heaven’s lights on.” Cas added, turning his laptop towards Sam, who leaned over.

 

“The British Men of Letters?” Sam asked with his eyebrows crinkled in confusion. He scanned the email quickly, but had to reread a few things to comprehend what he saw. “They’re asking us for information? I thought they were in the know when it came...to just about everything.”

 

“Apparently they’re just as clueless as we are. If there aren’t any monsters to fight, there’s not much for them to do; we’re likely a last resort. But this means this phenomenon isn’t limited simply to North America, it’s worldwide.” Castiel said, leaning back with his hands limp in his lap. He felt helpless in more ways than one. 

 

“Well, that’s just great. More questions, no answers. If I don’t get my hands on something to shoot or stab, I’m gonna lose it.” Dean said, Sam’s eyebrows rising. These past couple weeks, Dean had gotten more and more agitated. Normally his brother would have gone out and found a bar, or gotten laid, or something else to relieve stress, but he’d just stayed home and kept searching. 

 

“Dude, we’ll find answers, we always-“ Sam was interrupted by a grinning Jack appearing in the middle of Cas and Sam, scaring the daylights out of both man and angel as he looked between them both. 

 

“You guys have to come see this!” Jack cried, gripping both of their arms and vanishing, leaving a confused and frustrated Dean behind for a few seconds. At least until Jack returned and grabbed his shoulder, flying them all to the charred remains of Bobby’s house. 

 

Or at least, they  _ were _ charred remains. 

 

Before them, exactly as they had last seen it before it had been burned to the ground, was Bobby’s old place. Bobby was knocking on the wall next to his front door, Mary smiling and walking up to join him as Team Free Will was flown into the backyard. 

 

“What...how?” Sam asked, Dean just staring open mouthed at the place they had spent so much of their younger years in. Castiel was staring at Jack with a sort of wonder, not only on account of the house, but the feeling of flying again after so long without. 

 

“Jack...you did this?” Castiel confirmed, Jack nodding enthusiastically. Cas wanted to be proud, but he had to be practical first. “How? This goes beyond anything I’ve been trying to teach you.”

 

“Well, you taught me that angels have the ability to travel through time, and we’ve been working on healing animals at the shelters recently, which has been a huge help. But I talked to the nice lady at the front, and she said that a lot of older cats couldn’t get adopted, because everyone wanted kittens. So after practicing on some plants and objects first, I combined the ideas of healing and time travel, and figured out how to turn old animals young again.” Jack said, very matter of factly. 

 

“You...Jack, that’s  _ very _ creative of you, but time travel is a very messy business at the best of times. Are you sure you haven’t changed anything you shouldn’t? Pulled this house from another world, or something similar?” Castiel said, stepping towards the house and extending his grace to examine it. It felt like the regular house he had come to know; old, but full of comfort. 

 

“Pretty sure. I tested it a lot on books and fruit, made sure nothing felt...off. Unless I missed something, I should just be restoring objects and animals to how they were before they aged or were destroyed.” Jack said, smiling up at his progress, rightly proud. He had gone through everything he could think of to make sure there were no mistakes. 

 

“What about their memories? The cats, I mean. Did those get reverted too?” Sam chipped in, only half listening to the conversation as he felt the wood of the house’s back wall. Even distracted, his brain was reeling at the possibilities of this. 

 

Oh. Maybe he hadn’t thought of everything. 

 

“I...I guess I didn’t think of that.” Jack admitted, Castiel putting a supportive hand on his shoulder and giving a little smile. 

 

“I think, given it was only cats, and they likely would have been put down otherwise, we can overlook it for now. But humans and other sentient beings are more complicated than beasts, and memories are very important.” Cas told him, Dean letting out a little chuckle. 

 

“You would know first hand, wouldn’t you, Emmanuel?” Dean said, not looking away from the house as Castiel frowned. He didn’t seem to mean it in a cruel way, he seemed as distracted as Sam with the reappearance of Bobby’s place. The owner of said place opened up the back door and smirked at the men standing outside. 

 

“Y’all gonna wander around like a bunch of lost puppies, or do you wanna see if the cold beer in my fridge is still good?” Bobby offered, Dean cracking the first smile Castiel had seen in a while and leading the way in, Sam putting an arm around Jack and giving him a little squeeze to show he’d done a good job. 

 

Castiel looked around the yard one more time, breathing in the air with more sensitive lungs, thinking about how much had changed since they were last here. He went inside and joined them for beers, thinking now was as good a time as any to see if he could give himself human alcohol tolerance. 

 

____________________________________________

  
  
  


“I turn around, and poor Jack is trying to figure out how he’s supposed to wear the thing. Granted, it was definitely my fault for taking him anywhere close to the women’s underwear section, but I swear he was two seconds from trying to put it on his head.” Mary said, slurring her words slightly as everyone laughed, Jack smiling sheepishly as some back slapping and drunken chuckles were given. Everyone was pleasantly sloshed, the exploration of the house having revealed nothing to everyone but the old and reassuring walls and books. 

 

“I could do this all night if I were about a decade or two younger, but I think it’s time I plant myself in my old bed and conk out.” Bobby said, tossing his beer in the trash and walking over to Jack, holding out his hand, which the Nephilim took with some hesitation. “Thank you again, son. Mighty impressive stunt you pulled today, and I’m grateful.”

 

“I just wanted to help...you’re welcome.” Jack said, smiling. He was the only one who had been asked not to drink, especially because he was their ‘designated flier’, but he was having a great time regardless. “I’m glad Crowley was able to get you the land back, and everything.”

 

“Yeah, well...I guess the demon has a few good hairs on his head. Night all.” Bobby said, everyone wishing the old hunter goodnight as Dean sat at the kitchen table and thought about Crowley, his phone burning in his pocket. He knew the demon had told him to text him when he was ‘antsy’, and he’d been antsy for a while now. His tipsy mind told him a quick text wouldn’t be a problem, wouldn’t be admitting to anything...and if it ended in him getting properly plowed by the demon, he supposed there were worse things.

 

“I think Bobby has the right idea, it’s about time for me to pass out myself. Jack, could you take me back?” Mary asked, standing up when Jack nodded and going next to him, Sam finishing off his beer quickly and standing up to join them. He had been watching the newly drunken Castiel lean against the counter and make eyes at Dean all night long, with Dean recipericating once he’d had enough to drink. As the supportive little brother he was, he figured they could use a little time alone. 

 

“Pray once you want me to come get you both.” Jack said, and disappeared with his passengers, leaving the two other men alone. Dean looked up at Cas and gave a little tipsy smile, before the realization that they were alone sunk in, and he felt his stomach start to knot itself. The angel looked a little disheveled, his coat a little askew, his tie loosened, and a small smile on his face. Dean cleared his throat, finishing his beer and putting it next to all the other empty bottles.

 

“How ya feelin’, Cas? That humanity working out for you?” Dean asked, trying to distract himself. They’d been in this house plenty of times years back, but with Castiel leaning against the counter like that, he couldn’t help but remember one of the first times, where the angel had threatened to throw him back into hell. Maybe the years had tainted the memory a tad, but it was a pretty arousing event, if he was being honest. Not many people could put him in his place like that.

 

“It’s nice. I’ve never experienced alcohol that wasn’t used to dull pain or distract. It’s pleasant, like this. Is this why you drink? Maybe it has a different effect on angels.” Castiel said, looking thoughtful. Dean couldn’t help but give a little chuckle, thinking of all the times he’d abused booze over the years. Many occasions weren’t too nice.

 

“Nah, just depends on your mood. Depends on the people you’re with too, I guess. This is the first time in a long time I’ve actually had a good time with booze...first time I’ve drank in a while at all, now that I think about it.” Dean said, looking at the half full bottle of whiskey that was left, not adding that he hadn’t drank much in the last few months for fear of saying something about him and Crowley, or his feelings for Cas. The angel breathed out a little laugh, which made the hunter look up.

 

“That makes sense then. I like drinking with you. And your family, of course. Under good circumstances, like these.” Castiel said, looking at him softly, making a blush that Dean hoped could be blamed on alcohol creep up the hunter’s cheeks. The angel looked around, breathing deep and enjoying the sensations he was having, and how his fears were tempered by the drink. “It’s been a long time since we’ve been in this house...I don’t think I realized that I missed it. So much has changed.”

 

“Yeah. I gotta few more wrinkles now, Sammy’s hair is somehow longer, and you’ve changed your trench coat; it’s been a ride.” Dean said, getting up and starting to clear away the bottles, tossing them in the bin Bobby used for them. He gave the table a quick wipe down, trying not to focus on how alone he was with his friend, before feeling the hair on the back of his neck stand up.

 

“‘You should show me some respect...I dragged you out of hell, I can throw you back in.’” Castiel’s much too close and deep voice said, cold and dark, and Dean slowly turned to face an angel whose impossibly blue eyes were boring into his own, causing goosebumps to erupt all over him and plenty of blood to run south. The angel’s intense expression broke into a slightly dark smile, his eyes glittering with humor, and something else. “I used to be a lot more menacing before you showed me your world. My trench coat isn’t all that’s changed.”

 

Dean just gave a weak smile and a nod, trying to do everything in his power not to pop a boner in Bobby’s kitchen. Castiel made this impossible when he got even closer, one hand reaching out to grasp Dean’s shoulder, just like he’d always done, before lowering his hand to his bicep and squeezing gently. Dean swore the temperature in the room skyrocketed about ten degrees, and his eyes kept flicking between the angel’s hand and his eyes.  

 

“You don’t just have more wrinkles, you’ve gained some improvements yourself. Did you think I didn’t see the muscle you’ve been gaining? Your poorly kept exercising secret? You’re much... _ larger _ , than when I first met you, Dean. You were always attractive, but now you’ve filled in.” Castiel said, his voice not quite a whisper, and he was so  _ close _ , his eyes not allowing Dean to look away, his hand’s gentle grip keeping the hunter frozen. 

 

“Didn’t...uh...didn’t think anyone noticed.” Dean said, his casual and slightly shaky tone fooling no one, least of all Castiel. His cock hardened as the angel squeezed again. The angel was drunk, he clearly had thrown all memory of ‘personal space’ out the window. It didn’t mean anything...until a small voice in his head reminded him that no other angel had ever encroached on his personal space like Cas did. No angel, no person at all, treated him like Castiel did.

 

“I noticed, Dean. It’s hard not to notice, with you...” Castiel said, looking at every indicator of Dean’s arousal and want, checking both their alcohol levels to ensure Dean was coherent enough to make decisions, before he took a deep breath and opened his mouth. “...when all I want to do is  _ feel  _ your progress, to heal your sore muscles with my hands and grace. To drag you into the shower when you’re done and show you how much-”

 

Dean shoved him up against the counter faster than Castiel thought possible, his hand covering the angel’s mouth to stop him from talking, his eyes wide and panicked. Cas could feel his friend’s hand shaking, the heavy breathing against his skin, the feel of Dean almost between his legs. Years ago he had pinned Dean to a wall in much the same manner...he supposed this was payback.

 

“Stop. Please, don’t. Don’t-...don’t say that, you  _ can’t- _ ...” Dean tried, but clearly didn’t know what he was trying to get across. Castiel’s eyes just stared into his soul with lust and frustration and anger and...Dean was too close to avoid it any longer. He slowly lowered his hand, his voice breaking. “You can’t  _ want  _ me, Cas, I’m just...I’m not worth it.”

 

“Dean, do you think I would have done all I have, changed the way I have, for someone  _ unworthy _ ? You are...everything I want, that I  _ need _ . You’re not perfect, but you’re  _ mine _ . I knew you were special the minute I gripped you in hell, but never in my millennia of existing did I think I would fall, and fall  _ gladly _ , for anyone. You are worth everything, and I will show you that, if I have to spend another millennia doing it.” Castiel said, raising a hand to the back of Dean’s neck.

 

Cas only needed to push forward a few inches to break Dean, the hunter’s mouth opening and eyelids drooping when their bodies pressed against one another. Their noses were almost touching, but Castiel waited until the third time Dean’s eyes flicked down to his lips before moving in, the hunter accepting the kiss with a broken groan that had the angel’s blood igniting. Dean protested weakly with a concerned sound, pulling back slightly and not taking his eyes of Castiel’s mouth. 

 

“Bobby...” 

 

“Asleep and snoring in his bed. I’ll tell you if he wakes.” 

 

Castiel pushed Dean against the table as he latched his mouth onto the other man’s, the hunter enthusiastically returning the given kiss, wrapping his arms around his angel as they explored each other. Both groaned when Cas gripped Dean’s hips to pull them closer together, and Dean felt his hard cock start to leak, trapped between his leg and Castiel’s own member as the angel starting to work his tongue into his mouth. The hunter spared a thought for being glad he had cleared the table, but then Cas started to thrust gently forward, and all rational thought left him as two very hard and very trapped cocks started to enjoy one another’s company. 

 

Minutes passed as the two hungry men devoured each other like starving lions, Dean trying his best to put on a good show of aggression, at least until Castiel grabbed his ass and lifted him onto the table. God, the angel was acting like making out had been his livelihood for years, effortlessly moving him around and dominating him with his tongue, hands, and thrusts. The sounds Cas was getting from him would be embarrassing with anyone else, but this was  _ Cas _ , and he couldn’t be ashamed when the other man was making some deeper but just-as-eager noises.

 

“Oh, I’m sorry, I didn’t-” came Jack’s voice from behind Cas, both men breaking off their kiss as all the blood drained from Dean’s face, and every insecurity and fear and bit of self hatred inside him reared their ugly heads. How much had Jack seen? His erection went down, but he didn’t think he could stop his face from showing every emotion he was feeling. Both just stared at one another, breathing hard, unable to break off that last bit of contact. “I can come back, if-”

 

“No, we...we were just...talking.” Dean said, watching the light in Castiel’s eyes die, breaking something inside him as he hurt his friend. He tried to shake his head, pleading with his expression, but Castiel merely turned and took a few steps away, fixing his coat. Dean, looking so dishevelled that no one would believe the ‘just talking’ excuse, not even a two year old half angel, just slid himself off the table wearily. “You can take us home, Jack.”

 

Dean came and stood by Jack, a hand placed tiredly on his shoulder, but Cas needed a moment. He finished cleaning up the bottles still littering the counter, and gave the place an extra once over. Dean didn’t stop him, didn’t interrupt, kept himself quiet so he wouldn’t say anything else stupid. Finally Cas came and held Jack’s hand, and the three of them flew back into the bunker’ library, Dean retreating from the look he could feel both angelic beings giving him as he walked quickly towards his room, shutting and locking the door behind him.

 

It felt like he stayed there for an eternity, leaning against his door, his head buzzing as tears threatened to come to his face. He had kissed Cas,  _ Castiel _ , angel of the fucking lord, and the emotions were wrecking the inside of his head like a strongman with a sledgehammer. Guilt and relief and lust and regret and hope and something else he was desperately trying not to think about were all washing through him, and he was drowning. 

 

“Goodnight, Jack. We can talk more in the morning.” Castiel’s voice said on the other side of the door. Dean shut his eyes and nearly cursed. He heard Jack go to his room and shut his door, but Castiel...didn’t move. He was right outside his door, Dean could  _ feel  _ the angel’s eyes on it. It would be so simple. Open the door, resume making out, likely have amazing sex with his best friend. Instead his stayed silent, mentally kicking himself as he heard Cas eventually go to his own room, and close the door.

 

Dean lingered at the door for another few minutes, hoping beyond hope that Cas would just walk back over and kick the door down and have his way with him. But his message had been pretty clear when he had walked away without a word, and he couldn’t blame the angel. Crowley had been right, he’d been goddamn right about everything and now Dean was too much of a coward to-

 

The hunter thought about it for a moment, then a moment more. He and Crowley had made a bet, and here Cas was, essentially declaring his...feelings for him? Dean started to get angry, there was no way that was a coincidence. He pulled out his phone, dialing before he could get calm or rational thought enter his brain. When the demon answered, he sounded groggy, but Dean didn’t care. 

 

“What the hell did you say to Cas you son of a bitch?”


	12. Coming Out To the Family

**Summary for the Chapter:**

> Cas and Jack go on a little trip, and Dean has some secrets to share...

“And a happy hello to you as well, Squirrel.”

 

“Don’t fuck with me, you manipulative bastard, what did you say to him?”

 

“For one thing, I  _ have  _ fucked with you, and it’s been too long since then. For another, you’ll have to be a bit more specific. I can’t keep perfect track of every conversation I’ve ever had.” Crowley replied smugly, letting out a soft groan as Antonio sucked harder on his shaft, the king’s blissed and relaxed attitude not much fazed by an angry Winchester. They were always mad at him, after all. 

 

“Are you...are you jacking off?” Dean asked, thrown, lowering his voice even lower than it already was. The thought of Crowley touching himself on the other end of the phone, especially after the night Dean was going through, was a mixture of frustrating and hotness he didn’t need right now.

 

“Actually, Antonio’s been swallowing my cock for the past twenty minutes. After he ate my ass for nearly an hour. He’s quite good at it, I’m interested to see if you’ll agree.” Crowley said, eyeing the naked demon between his legs up and down and appreciating his lack of gag reflex as he went balls deep on his monster cock. “Can’t decide if I want to reward him with my ass, or pin him to my bed and make him scream on my cock. What do you think?”

 

“Crowley, I’m going through something right now, something  _ important _ .” Dean growled, annoyed that his cock was half hard and only getting stiffer when he heard Crowley give a low and pleasured chuckle. He couldn’t help it, he’d been worked up for ages with no relief...or at least, that’s what he told himself.

 

“Very well, Dean, I’ll bite. What did Castiel say or do that makes you think I spoke with him?” Crowley asked, and Dean was...silent, for a very heavy minute. Well, heavy for Dean, Crowley had his hand on the back of a hot demon’s head and was lazily thrusting up into his gullet, and let out a groan. “You can either tell me what this is about, or I’m going to hang up so I can give this stud a proper pounding.”

 

“He kissed me. Among...other things. Not...not sex, just...I need to know if you said anything to him, if you...Crowley, I need to know if you forced him into this somehow, for our bet. I can’t...if you did something, I don’t know what...” Dean tried, losing traction and sliding down his door, putting his hand on his forehead and trying to keep it together. If this was all a trick, if it was all just for some bet...the sounds of sex and moaning stopped.

 

“Don’t give me that look. Go get the toy, the blue one, and open yourself up for me. I’ll just be a minute.” Crowley said, his voice sounding distant, before coming back to full volume. “Dean, Castiel called  _ me _ , after he heard you and I making a bet and discussing past ‘adventures’ over the phone. When are you going to realize you live with supernatural beings that can hear through walls? Assuming you’re both in the bunker, he can probably hear you as we speak.” Crowley said, Dean paling and his mouth opening slightly, no sound coming out, and the demon sighed.

 

“I told your angel to take a little time and get back at you for all the damned waiting you’ve made him do. The sappy featherhead didn’t even use half the time I gave him. He wants you, you bloody idiot, and he kissed you because he  _ wanted  _ to. And for the record, it doesn’t sound like he minds sharing, so I expect you to be on your knees and bloody grateful when you finally work through all that internalized homophobia.” Crowley said, peeking over at Antonio gently thrusting the long blue dildo inside himself. Long and thin, so the king of hell could enjoy truly stretching him out. 

 

“He, um...” Dean said, trying not to have an actual panic attack. This was worse, this was so much worse. Cas  _ liked  _ him, Cas wanted to  _ kiss  _ him, and he just _ let him go back to his room alone _ . Another, less horny part of Dean knew that Cas liking him was bad for other reasons, like how most people close to him died horrible deaths, but that didn’t seem as important. 

 

“The angel has a bit of a thing for you, Squirrel. Only been for about a decade, it’s probably time to climb out from under that rock and notice. Now, I’m going to go fuck some ass. I suggest you go get some as well, or whatever it is you want to do with him and that trench coat.” Crowley said, hanging up and pumping his cock with his other hand as he walked back to the bed and his waiting lover. “Spread those thighs wide, little boy. Daddy’s ready to play.”

 

Dean just lowered his phone slowly, feeling like he wanted to melt into the floor. Cas had heard his bet with Crowley, he knew he liked men...had he heard what had just been said? Was his hearing that good? This...there was no other way to look at it, Castiel had kissed him because he wanted to. They had been drinking, some, but he couldn’t use that as an excuse any more, not after this. Everything that had happened lately started to make more sense, and he felt like an idiot for not seeing it sooner.

 

The hunter froze when he heard the sound of a door opening, his heartbeat picking up. That was Castiel’s door, he was sure. It had this particular squeak that Dean kept meaning to fix, but kept forgetting. He heard the angel walk slowly to his door, tears coming to his eyes as he heard Cas stop and stand right in front of it. Less than two feet between them, blocked only by a door.

 

“Did you...hear all that?” Dean asked, his voice so quiet and his head hung so low that no one outside his room should have even known he was talking. There was silence for a moment, and Dean counted the seconds.

 

“I did.” Castiel’s low voice muttered back, and Dean hoped that everyone else was too passed out to hear anything. If any of them came out of their rooms to find Cas talking to his door...god, what would they think of any of this? Would they hate him? Sammy didn’t seem to have a problem with Charlie or those gay hunters they met, but would it be different with him? And mom and Bobby were from a different time entirely. Would they judge him, not want to see him again? The fears swirled around his head savagely, and he gently thunked it against the door to shut them up.

 

“I don’t...don’t know what to do, Cas. This isn’t like with Crowley, this isn’t just a...tumble in the hay between buddies, it’s...it’s you and me. I can’t hide that, not if we...what’s everyone going to think? What if you realize later on that I’m not good for you? And you’d be  _ right _ . I can’t even say any of this to your face, Cas. I’m fucking terrified, and we fight monsters for a living.” Dean said, keeping his voice at almost a whisper, feeling himself shaking. There was no response, and for a second Dean thought Cas had left, until the angel sat down and leaned against the door opposite him, the hunter feeling the weight of his friend press against the wood.

 

“What can I do?” Castiel asked, and Dean swallowed roughly. There he was, like always, trying his best to help him out. He was always there, and Dean was finally starting to realize part of the reason Cas was so damn loyal. The Winchester thought about what Crowley said, wondered if he should just let the angel in and finally have what he’d wanted for so long. But...his fears wouldn’t let him be.

 

“I...Crowley’s bet aside, Cas, I don’t know how long I’d be able to keep something like this from everyone. Especially Sammy. He probably already knows something’s up, knows me too damn well.” Dean said, shaking his head with a sad smile, then sighed. He shouldn’t need their approval, not with everything his family had gone through, but...he did.

 

“I don’t know if Crowley meant the whole ‘decade’ thing, but I know I’ve probably kept you waiting for...a while. Too long, for both of us. But I can’t just rush into this. I need to know if they’re OK with...that. Guys. Me. Guys  _ and  _ me. Sorry, I know I’m not making a lotta sense. Can you give me a little more time? A couple days to think and...talk to them?” Dean asked, frustrated that he couldn’t just give Cas what he wanted. He deserved it, they both did.

 

“I’ve been patient for close to a decade now, Dean. I can handle a couple more days...I’ll let you get some sleep.” Cas said, sounding a little frustrated, but agreeable as he stood up, Dean rising as well and staring at the door as he heard Castiel hesitate. “I really enjoyed tonight, Dean. Very much. I want to do that with you again, and more, whenever you’re ready for it. I’m going to take Jack on a bit of a field trip tomorrow, and give you and your family some space.”

 

“Thanks, Cas. I’ll...I’ll let you know.” Dean replied lamely, cringing as he heard Cas walk back to his room. He leaned his forehead against the door and thumped it a few times in frustration, then realized Castiel could probably hear that...and whatever else he said. “I enjoyed it too, Cas, like you wouldn’t believe.”

 

He hoped the angel heard that, and he started pacing slowly back and forth his room, scratching at the stubble on his face and thinking. How was he going to ask his family about this? One at a time? All together? Should he just...’come out’ to them like he’d seen in a few TV shows? Tell them this was the way it was, and they could deal with it? Or ask them if they were alright with gay people, and just slowly lead up to it? He must have been pacing for quite some time, because his phone’s text alert went off, and it was nearly one in the morning. 

 

_ Dean, do you want me to help you sleep, with my grace? I can’t knock you out from here, but I can make you tired, without coming in. I know you normally shun that kind of help, but you’re stressed about tomorrow, I can tell. Sleep will help you make better decisions in the morning. -Castiel _

 

Dean thought about it. He did normally make better decisions after he slept. And sleep didn’t feel like it was coming any time soon, with all the stress he was feeling. He thought about Sam and everyone else, how he’d look if he was haggard and exhausted, trying to ask them weird questions. He needed a good night's sleep, and Angelic Ambien sounded like a pretty solid way to get one. 

 

_ go for it _ , he texted.

 

_ Lie down on the bed _ . Cas replied, and Dean obeyed, feeling a little giddy doing so. Cas was gonna use his grace on him from another room. He wondered if the powers of heaven could be used for other things, like when Crowley did things to him, and what the limits were. Those thoughts were slowly quieted as Dean felt a powerful wave of sleepiness overtake him, and he yawned loudly. His phone went off one more time.

 

_ Goodnight, Dean.  _

 

And he drifted into peaceful darkness.

 

______________________________________________________________________________

  
  
  


“Thank you, Megan.” Castiel said to a cute redhead as she smiled and walked away with an orange tabby in her arms, off to put the kitty away in the back. They’d already met the shelter employee several times this month, as Jack practiced healing and other benevolent powers on the animals there. “We can go in. I’m still shocked Sam managed to find someone like her so close.”

 

“Are good witches very rare?” Jack asked, following Castiel into the back of the shelter, which was thankfully closed today. Megan would allow Jack to practice whatever he needed to on the animals, so long as none were hurt, and Sam had promised to let their group of hunters know that, while a witch, she was a good one, and was not to be messed with. 

 

“Somewhat, though my opinion is that they simply are less likely to cause problems. They don’t sacrifice their souls or morality for power. And because they use their magic for good, they’re less likely to be corrupted or attract hunters.” Castiel said, Jack nodding as he understood. Rowena seemed to be somewhere in the middle of the two, but Jack liked her. She was helpful.

 

The two angelic beings made themselves at home with all the barking dogs and meowing cats in the back, a few other less common creatures like snakes and rodents kept separate. Megan wasn’t the owner, but given her fantastic ability with animals, she’d been given a lot of leeway to do what she wanted with the design and operation of the business. Everything was clean, well organized, and half full of happy and mostly healthy animals. Castiel led them to where Megan had told them the old dog that had been dropped off was, and Jack started to warm up his grace.

 

“So...now that you think you and Dean might, you know...be together, does that mean we’ll need to stop doing...stuff?” Jack asked, trying and failing to sound casual. He and Cas had only jacked off together once more after their first time together, and he hated the idea of stopping, even if they hadn’t actually had any sex yet. 

 

“I’m not sure. Dean...hasn’t exactly been forthcoming with details. I’m hoping that we would still be able to, after, but it’s too soon to tell.” Castiel said, opening up the dog’s cage and smiling when the old golden retriever limped out of his spot to receive some gentle pats from the angel. “Hm...old, fifteen years or so, and some problems with his kidneys. Sit?”

 

The dog sat obediently when Castiel said it again a few times, lying down at another command. This was what they were hoping for, an animal who knew tricks, so that Jack could focus on leaving the dog’s memories intact while still returning its youth. Castiel kept his hand on the dog’s head, monitoring all the dog’s vitals while Jack raised his own hand, his eyes glowing gold. A gentle, yellow light poured out of the Nephilum’s hand, bathing the animal, who yawned.

 

“Good, very good. Concentrate, keep his essence the way it is right now. Now turn the years back, slowly.” Castiel instructed, keeping careful watch, the dog slowly growing slighter and healthier, panting happily. Jack had already learned to make the experience feel like nothing was happening, to not startle the animals, and it wasn’t long before the Castiel had to kneel down further to keep his hand on the retriever’s head, as he was now a puppy.

 

“I...I did it, I think. Are his memories all still there?” Jack asked, slightly concerned as he lowered his hand. It wouldn’t be the worst thing if the dog didn’t have them, they weren’t quite as valuable as a human’s, but the dog had still had love and affection in his life, and he wanted all that to still be there. Castiel got up, the puppy looking at him and wagging his tail, still lying down.

 

“Sit. Good boy! Now lie down? Very good! Jack, I think you did it!” Castiel said, smiling brilliantly and reaching down to pick up the puppy, examining him with his grace carefully, finding nothing out of place. “All there, every hair, cell, and memory. Well done.” he continued, looking proudly at the young man, who came over to half hug the angel as he pet the dog.

 

“Can I go show Megan? I want to ask her what other animals I can help, then...maybe we can go celebrate? If you’re alright to, since Dean is still...deciding?” Jack asked hopefully, Cas smiling and looking the Nephilim up and down when he took the puppy. How could he say no to that look?

 

“For now, since we’re waiting until his family gives their opinion, I thought it would be a good chance to get a hotel room and see how many different ways there are to have fun that don’t involve actual sex. How does that sound?” Cas asked, Jack grinning and running off to show Megan, so they could finish quickly. The angel just looked around the place, at all the animals healed here through magic and grace, and leaned against the table. He hoped Dean was alright, but this was a good distraction in the meantime.

 

______________________________________________________________________________

  
  
  


“‘Sammy, I like Cas.’ No, ‘Sam, what would you say if Cas and I started-’. Damn it, why does this have to be so hard?” Dean asked, looking at himself in the mirror and checking he looked sufficiently not crazy. He was pretty sure he passed. Barely. The good night of sleep had helped; whatever Cas had done had kept any stressful nightmares away. 

 

The hunter opened his door, feeling silly as he looked both ways to make sure mom wasn’t present, since she was splitting her time between Bobby’s house and here. Sam had to be first; if he wasn’t alright with it, he couldn’t imagine anyone else accepting it. He made his way to the kitchen, not quite sneaking, but close to it. Sam was there, on his tablet, sipping a cup of coffee.

 

“Morning...hey, check this out. You know how there were some witch sightings for a while after everything else disappeared? Well now, apparently, the only ones anyone is finding are witches that, as far as we can tell, aren’t evil. Like Megan, that one that’s helping Jack out with stuff.” Sam said, not looking up until Dean’s silence caught his attention. The older Winchester jumped a little, then walked over to the coffeemaker to get some, even though he wanted whisky. Not till after, he told himself. 

 

“Yeah, that’s uh...that’s weird. But, you know, at least it’s the good ones, right? We better tell Rowena to keep her nose clean.” Dean said, smiling too wide, his brother’s frown letting him know it looked as uncomfortable as it felt on his face. He sipped at his too hot coffee and tried to remember what he practiced in the mirror.

 

“Yeah...right. You alright, dude? You’ve been a little out of it lately, are you going stir crazy or something?” Sam asked, and Dean looked down at his coffee like he wished he could dive into it and disappear. Or drown. He was right, his little brother knew him too well. He cleared his throat, stroking his cup with his thumb as the silence grew.

 

“Can I...talk to you about something? It’s, uh, not case related.” Dean said, Sam shutting off his tablet and turning, nodding. He swallowed, not sure how to start, or if he should lead up to it, or just...rip off the bandaid. “You know how...or when the, uh...like with Charlie and that fairy, Gilda...”

 

“...is this about you and Cas? Last night, maybe?” Sam asked, smiling a little at his brother’s awkwardness while Dean gaped like a fish. “Knew I made the right choice, leaving you guys alone. So? How was it? How far did you get?” he continued, getting up and casually strolling over to the think to wash his cup.

 

“You, you know? The hell, man? How?” Dean demanded, almost angry. It was better than Sam being angry, or judgemental, but  _ he  _ hadn’t even known until last night. “And nothing  _ happened _ , we just...we kissed for a while, and I sort of...ran off.”

 

“Oh, dude, seriously? Wow. You guys have been after each other for years, I thought Bobby would have had to remodel his kitchen or something.” Sam said, and Dean slumped against the counter, setting his cup down and wiping both hands down his face. “Were you worried? About how I’d react? You know you’ve got nothing to worry about, we’ve kind of stopped a few apocalypses together. Kinda thought you liked guys, even before Cas.”

 

“I just...dad always made it seem like one of those really bad things, you know? Kept calling them fairies and queers and stuff, and I didn’t...I didn’t want to be like that. It’s not like I don’t like women.” Dean clarified, and Sam nodded as he leaned next to him, rolling his eyes to the sky.

 

“Trust me, Dean, if anyone knows how much you like women, it’s me. How many viruses has my computer gotten over the years from ‘Busty Asian Beauties’?” Sam asked, glad when his brother smiled, and put a hand on his shoulder. “You can like both. I even did a little experimenting at Stanford, it wasn’t half bad.”

 

“ _ You _ ? Really? Geez...am I the only one who’s new to this? Even Cas seemed like he knew what he was doing. Though, I guess that coulda been because of Meg. I didn’t expect you to be so alright with this, I don’t know what to say.” Dean admitted, relief washing over him in waves. His brother was good with this, that was the biggest hurdle. Anything else he could handle. 

 

“What made you wanna tell me? Just that something finally happened? Wait, was that your first time doing  _ anything  _ with a guy?” Sam asked incredulously. He assumed maybe there had been some stuff going on when he wasn’t looking, at least, even if it wasn’t with Cas. He was pretty sure his brother had a bit of a thing for cops and other men in uniform, and they dealt with a  _ lot  _ of those in their line of work. 

 

“I mean, I’ve always thought about it, but lately there have been things...” Dean said, uncertain if he should tell Sam. Technically, he had lost his bet with the king of hell, and even though he hadn’t actually signed anything, he felt a little honor bound. “Don’t laugh, but...Crowley? Last month, after he helped us out, we kind of...messed around.”

 

Sam looked like he tried, he looked like he tried really hard. And really, he did. But the laughter started, and it didn’t fucking  _ stop _ . Dean turned absolutely beet red as his brother started out small, and eventually was doubling over and laughing loud enough to wake the dead. Dean folded his arms and tried to wait it out, but every time his brother looked at his embarrassed face, Sam started all over again. 

 

“ _ Dude _ , come on, it’s not...it’s not that funny.” Dean insisted, which just set Sam off again, who looked like he was about to start crying at this point. Dean wasn’t actually sure he had ever seen his brother laugh this much, and it was a weird mixture of cute and infuriating. 

 

“After...after all the shit you gave me for Ruby, you...” Sam had to pause for a moment to control his breathing, getting himself a glass of water. “You go, and you bang the king of hell. Oh god, this is priceless. You’re my brother, and I love you, and support you, but jeez man,  _ Crowley _ ? What were you thinking?”

 

“OK, first of all, I stand by the whole Ruby thing. Crowley’s...different. He’s helped us out, a lot, and...he’s not bad looking. Yeah, he’s an asshole, but he’s kind of a...charming asshole.” Dean said, Sam shaking and trying not to let his laughter out again, and Dean knew he was just digging himself a bigger hole. “Look, point is, you’re alright with this, now we never have to talk about it again. Ever.”

 

“Talk about what?” Mary said, walking into the kitchen with a backpack slung over her shoulder, Dean’s face draining a little of color as she made a beeline for the coffeemaker. “Gonna be heading out to Bobby’s for the day to help him sort some things out, and I could hear Sam laughing while I was packing, something funny happen?”

 

Dean’s mouth wouldn’t make sounds. He kept trying to say ‘good morning’ or ‘nah, nothing to worry about’ or freaking ‘hi’ and nothing would come out. Sam noticed Dean’s distress, and gave him a sort of questioning look, before miming to him in their weird, brotherly language ‘do you want me to tell her?’. Dean thought about it for a minute, realizing his mom would likely be gone for more than a day, and this was the best chance he had to tell her. He nodded to Sam.

 

“So, mom. Weird question. Do you remember when I was telling you about all the big stuff that’s happened in the world while you were gone?” Sam asked, Mary finishing pouring some cream into her drink, nodding as she put it away.

 

“Of course. You miss a few things when you die and come back, decades later. Why? Something else big happen?” Mary asked, sipping at her coffee, her eyes flicking between her two boys. Dean looked like he was gonna be sick, but Mary knew better than to push. Dean was more like her in a lot of ways, guarded, and pushing didn’t always help. 

 

“Well...kind of. You know how I told you how about five years ago, gay people could get married? That it was legal?” Sam asked, Dean wanting to kick himself and Sam and Cas and everyone who got him into this mess. Crowley too, now that he thought about it. Bastard would probably like it and claim he had a kicking fetish or something. 

 

“Yes. They didn’t revoke it, did they? I still haven’t looked up Marge to see if her and her girlfriend ever got married. I keep meaning to, but I don’t think I’ll ever get the hang of Facebook.” Mary said, frowning at the thought of one of her old friends not being able to be with the one she loved. Assuming they were still together, or alive. It was hard reconnecting with people, being dead for so long.

 

“What? Who’s Marge?” Dean asked, finding his voice and feeling hopeful. Mary finished taking another sip before putting her cup down. Sam was just sipping at his water, watching his brother realize that their mother was more with the times than he had known. 

 

“One of my old highschool friends. I drove her to her girlfriend’s house when her parents kicked her out. I wish I could call her, but it’s probably best not to broadcast the ‘I’m back from the dead’ thing.” Mary said, thinking back on her old life. There were things she missed, and things she didn’t. Old friends lost, new ones gained.

 

“So...you don’t have an issue with...people like that?” Dean asked, getting nervous again. Mary just shook her head, looking confused. “So, if, you know...Castiel, Cas and I, we uh...if we started...if we...” Dean tried, unable to get the full sentence out, and Mary looked even more confused than before. 

 

“I’m sorry, are you...is he  _ not  _ dating Castiel, already?” Mary asked Sam, who choked on his water as he started laughing, Dean’s mouth dropping open as their mother looked worriedly between them both. “Did I misread things? Bobby and I were pretty sure you must have started dating after he passed away.”

 

“No! We just kissed for the first time last goddamn night! And  _ you _ , stop laughing!” Dean ordered his brother, who just kept laughing more, Mary blushing a little when she realized what Dean must be going through. She had assumed he just didn’t want to talk about it, or maybe they weren’t ‘out’ yet, and hadn’t wanted to push. Maybe pushing had been a better idea, in this case.

 

“Sweetheart, I have absolutely no problem with you dating Castiel, or any man, so long as you make each other happy.” Mary said, walking over and giving her anxious son a big hug. Dean deflated after that, relaxing into her arms, Sam’s hand finding his shoulder again. “Never be afraid to talk to me about things. We go on monster murder trips together.”

 

“Well...we did. Before they all vanished.” Dean pointed out, and just like that, the Winchesters started talking about the job again. Dean was a little quiet, relishing in the fact that he apparently had nothing to worry about, but just enjoyed the sound of his mother and brother discussing the limited number of details they had found. Once his mom left, Dean ate breakfast with Sam, worked out for a while, and worked up his courage. Then, he pulled out his phone to text Cas...

 

______________________________________________________________________________

  
  


Castiel, at the time he received said text, was sliding his hard, slick cock over Jack’s entrance over and over again, as the Nephilim groaned and thrashed face down underneath him. The angel wasn’t penetrating him, just using his asscheecks as a lovely spot for his cock to slide between. Both men were naked, having stripped themselves out of restrictive clothing an hour ago, and Cas’s tan and muscled torso was covered in sweat when he reached over to grab his phone, not stopping his idle thrusting. 

 

_ mom and sam both sort of knew, went well. can we talk tomorrow? _

 

Cas smiled as he replied, squeezing Jack’s ass with the other hand and causing a pleased noise from the boy. They had looked up ways to have fun without oral fun or penetration, and so far it had been amazing. The angel was surprised by how easy sex came to him; just do what feels good for you and your partner. And right now, with one day left before him and Dean discussed anything, he was feeling pretty damn good.

 

_ Of course. Jack and I will be back in the morning. We might need to have a conversation with him as well. _

 

Castiel tossed the phone onto the bed and put both hands on Jack’s hips, practicing his thrusting for when he was hopefully able to do this to Dean’s ass. The sweat and precum made their motions loud and filled the room with the smell and sounds of sex. Jack had already cum twice, once by his own hand as he and Cas just jacked off next to each other, another with Castiel pumping his cock and playing with his balls. He was limp and plient under the older angel, who was all too happy to play with the younger man’s gorgeous form.

 

“Dean says I can talk to him tomorrow, that it went well. Which means we have all day, and all night, to do whatever we want.” Cas said, gently pushing Jack until he was flat on the bed, his hard cock trapped under him. The angel got back on top, grinding against the Nephilim’s ass and humming in satisfaction. “This feels amazing for me, are you enjoying it?”

 

“Really good. By myself, I only ever thought my penis could feel good, but you rubbing against my hole like that...are you sure you can’t put anything in me? If it feels anything like this, I want to try it.” Jack said, breathing hard. Cas had gotten him off twice, but the angel had only cum once himself, and Jack didn’t want to be greedy, but it was all feeling so good. 

 

“Be patient. I’m hoping Dean will be interested in something of an ‘open relationship’, where both partners are allowed to sleep with other people, but we’ll have to see. I’m alright doing this now, since we aren’t actually in a relationship yet, but if we do, then what Dean wants come first.” Castiel said, kissing the back of Jack’s neck a few times and running his hands up and down the Nephilim’s sides. “Turn over, I want to kiss you.”

 

Jack eagerly flipped over, both groaning when their cocks were ground together, quickly diving into each other’s mouths as they slid against each other. Castiel dominated the kiss, grinding down and moving Jack where he wanted with his hands, none of which was complained about. Castiel thrust in time with his tongue, giving Jack dual stimulation, but finding his own orgasm starting to rise when Jack slid his legs around the angel’s driving hips.

 

“Jack, I’m getting close. Can I cum on you?” Cas asked, Jack just moaning and nodding, and Cas picked up the pace. Jack surprised him by going after his neck the same way Cas had once done to him, the boy’s tongue forcing loud groans out of the angel as he thrust a few more times to reach his peak. “ _ Fuck,  _ Jack, _ yes! _ ”

 

Castiel began to absolutely soak both of their already wet bodies with his huge load, each thrust shooting more and more sperm all over his eager partner. He cried out in ecstasy as his muscles burned and squeezed cum from his depths, Jack moaning as everything became so much slicker, his own orgasm forced from him a moment later, causing him to scream and help Cas paint their bodies in white. 

 

“That felt so, so good. I can’t believe actual sex is going to be better than this. I really, really want to do it with you and Dean. I don’t even care how, who goes where, or how any of that works. I just want to do it.” Jack said, five minutes later, as Castiel panted on top of him while they both recovered. The angel smiled, brushing the sweat-dampened hair from the boy’s eyes.

 

“If Crowley is right, I think Dean will be very pleased by the idea.”

**Notes for the Chapter:**

> I know it's still about a week away, but Merry Christmas to everyone!!


	13. Finally

**Summary for the Chapter:**

> Dean and Castiel...resolve things. Passionately.

**Notes for the Chapter:**

> So sorry this took so long, the holidays have been busy. Originally I was going to have other plans for this first time, but I did what felt right. Hope you like it!

Dean was spending about five times as long in the bathroom as he usually did.

 

He had already shaved his face, twice, and showered for almost half an hour. Now he was messing with his hair, trying to get it just right, and feeling like such a girl while he did it. But Cas and Jack were on their way back, and while he wasn’t sure what exactly was going to happen, he knew he needed to be ready. Or, as ready as he could be.

 

Dean had broke down and fingered himself in the shower, trying his best to get himself clean, and ignore the incessant bobbing of his aching dick. The urge to crank one out was powerful, especially because it would clear his head, but he wasn’t sure he actually wanted to clear his head. Besides, what if something happened? ‘ _ Oh, gee Cas, I’d love to have sex, but I got impatient and choked my chicken in the shower _ ’.

 

Getting dressed was even worse. How were you supposed to dress when you talk to your...Dean supposed ‘crush’ might have to be the best word, but it sounded so juvenile when applied to a warrior of heaven. He had all sorts of uniforms, and plenty of hunter regulars, but none of them felt right. He needed to get some regular ‘going out’ clothes, or something. The Winchester panicked a bit when he heard the sounds of arrival, throwing on a basic black shirt and a light blue plaid overshirt-which did not match at _all_ -before stepping out of his room and messing with his hair as he walked. 

 

Castiel and Jack got to him before he could leave the hallway, just as he turned a corner. Both were carrying bags, smiling as they joked about something, and then the hunter and angel saw each other, and everything just seemed to stop. Dean saw Cas in a new light, one where things weren’t one sided, where he knew what his best friend’s mouth felt like. And Cas...well Castiel was just thrilled that Dean couldn’t help but look at him like that. Meanwhile, Jack looked between the two, realization dawning on him.

 

“So this is what Sam was talking about.” Jack said aloud, both other men finally breaking off their prolonged eye contact to stare at the younger man in confusion. “It’s nothing, just learning new things every day. I know you guys need to talk about stuff, so I’ll be in my room if you need me.” he continued brightly, smiling at both of them before walking off towards his room.

 

“Did you...did you tell him?” Dean asked, once the Nephilim was out of view. Probably not out of hearing range, Dean reminded himself. He needed to remember about super hearing, outside of stalking vampires. Castiel just gave the hunter a Look.

 

“Dean, he found us in a rather compromising position. If I hadn’t told him, he still would have known, just been confused. And aroused, apparently. Do you mind if I...?” Castiel asked, holding up his bag, Dean quickly getting out of his way and letting him pass, leaning against the wall and shuffling his feet a bit. “...Dean, you can come  _ with  _ me. Unless you’re afraid to be in a room alone with me.”

 

“Ouch. I suppose I deserve that...sorry I reacted the way I did, running off like that. I really thought people were gonna, you know, freak out about this if they found out. Mom thought we were already a thing, so apparently I’m not as subtle as I thought.” Dean admitted, walking side by side with the angel to his room. His heartbeat wouldn’t slow, no matter how carefully he breathed, and he was pretty damn sure Cas could hear the traitor.

 

“You aren’t, but...I know you pretty well after all this time. I didn’t want to push you, to put you in a situation you might regret later.” Castiel said, putting his bag down and turning to his friend, looking him up and down. Dean couldn’t get himself all the way through the door, leaning ‘casually’ against the doorframe like he wasn’t close to pissing himself. “Where are Sam and Mary?”

 

“Mom’s helping Bobby settle back in; talking about moving in with him full time, actually. Sam made some excuse about checking on a few leads, won’t be back till tomorrow. Pretty sure he just wanted to give us space.”

 

“I see...well? What happens now?”

 

“Whataya mean?”

 

“Well, does this mean you’re comfortable talking about things? That we can be open with one another?”

 

“Yeah, yeah man, I’ve had your friggin tongue down my throat.” Dean said, swallowing and forcing himself not to relive the memory too vividly. “Pretty sure I can handle some talking.”

 

“Very well.” said the angel, sitting down on the bed, facing Dean.

 

“For the better part of a decade, I’ve had...feelings, for you.” Cas started, nervously looking at the bed and smoothing over non existent wrinkles. He forced himself to look back up at Dean. “When I first started to get to know you as more than just the ‘Righteous Man’, I didn’t realize what these feelings were. It’s not part of who an angel is  _ supposed  _ to be, and it took me a very long time to understand them. I’m still not sure I do. Took me even longer to realize that you might feel the same way. That is...if you do, if this is more than just physical attraction for you.”

 

“It is.” Dean said immediately, going a little red, but Cas’s smile made it worth it. “I...geez, Cas, that’s a lot.” he continued, folding his arms and finally entering the room properly, pacing as he tried to not say something stupid. Thankfully, Castiel was patient. “When I met you, sparks flew...forget I said that, that’s cheesy as hell. I am  _ not  _ good at this kind of thing.”

 

“Take your time.” Castiel said, nodding at the bed. It took another minute of pacing before Dean hesitantly joined him, keeping only a few inches between them. He wanted to touch Cas, but he wasn’t sure he would stop once he started.

 

“Sorry. When I...well, when I  _ first  _ met you, I stabbed you, and you knocked out Bobby, so, not the best introduction for either of us.” Dean said with a wry smile, Cas joining him as he recalled. “The attraction was always there, at least for me, but...I think the first time I looked at you, like  _ really  _ looked at you, was after that damn brothel.” Dean said, smiling and looking down at the floor as he remembered Cas, tie askew, a hooker fleeing before him. “You made me laugh...right when I needed it.”

 

“It wasn’t exactly my intent, but I’m glad I did. I like seeing you smile.” Castiel said easily, Dean keeping his eyes on the floor as the blush crept up his neck. The angel could tell how nervous the hunter was, could practically feel the anxious energy coming off the other man, and put his hand gently over Dean’s. “I know this is new, and a little foreign to both of us. I’m nervous too. If you don’t want to do anything...physical, for a little while, I can wait...”

 

“...but?” Dean asked, hearing the hesitance in Cas’s voice. He looked up into his friend’s eyes, and swallowed a little when he saw the look in them.    
  
“But I would very much like to kiss you. And anything else you think you’re ready for. I know you’ve...done things with Crowley, but not the details.” Castiel admitted, and Dean grimaced, rubbing the back of his neck. Crowley really liked to gloat, and him and Dean had done a lot of things already.

 

“Does that make you mad? That I did stuff with him? He’s a demon, and kind of an ass sometimes.” Dean said, uncertain how his friend would feel. Castiel surprised him with a light chuckle, and he felt warm at the sound of the angel’s laugh. Cas turned towards him, putting a reassuring hand on his shoulder. 

 

“Dean, monogamy is much more of a human trait. I have no issue ‘sharing’ you, as Crowley put it, so long as you’re happy. And besides, did you forget when I made out with a demon in front of you? Next to you, Meg is one of the only people I’ve felt romantic feelings for. And I’m quite certain she knew of my feelings for you; you were brought up quite often while my mind was...altered.” Cas said, Dean recalling the demon’s ‘he was your boyfriend first’ comment and nodding. “I’m not going to judge you, Dean, if you won’t judge me.”

 

“She  _ was  _ a pretty smokin nurse, I’ll give you that. But...seriously, Cas? You would be alright if I did things with Crowley, even now?” Dean asked, still surprised when the angel nodded. “I mean...geez, dude, that’s pretty different.”

 

“Well, do you think you would be accepting if I ever did things with others? I would be more than content with just you, but your situation is different. All your life you’ve had women, and I don’t want you to feel you have to give them up to be with me. You’ve had enough sacrifice in your life.” Castiel said, sliding his hand up to the other’s neck. Dean turned towards his friend a little more, putting a hand over the one on his neck, trying to breathe evenly as his excitement rose.

 

“This from the guy who’s given up heaven for me, more than once? I can’t promise I won’t get a little jealous, Cas, but I can do the whole ‘open’ thing if you’re up for it. You haven’t exactly had a lotta experience, last I checked, and I don’t want to stop you from having a good time. Maybe you can...let me know?” Dean asked hesitantly. The angel nodded, lowering his hand gently down the Winchester’s chest, making the other man shudder.

 

“Communication. In the interest of openness, then, you should know that I got together with an attractive young man, recently, when I realized things might be getting more serious between us. Part of the reason being...I wanted to practice. No actual intercourse occurred, but...shall I show you what I learned?” Castiel asked uncertainly. He expected Dean to get annoyed, maybe mad, but the hunter just nodded with slightly wide eyes.

 

This kiss was different than their first. It was slower, more careful. Both kept their eyes open for a while, exploring gently, only shutting their eyes when Cas finally slipped his tongue inside. Dean’s hands came up to the angel’s face and neck, while Castiel slipping his hands down to grip his sides. Dean shook slightly as the Cas broke off the kiss a second later, standing and sliding off his trenchcoat. Dean stood as well, gripping his flannel.

 

“Should I...?” 

 

“I want to be naked with you, unless you want to wait.” Castiel said, his fingers stilling halfway down the buttons of his shirt. Dean nearly ripped his shirt as he removed it, Cas grinning and watching as he continued to unbutton. The hunter pulled off his tshirt, feeling self conscious even as Castiel’s eyes looked at him with need. He hesitated with his jean’s as Cas got off his undershirt, both of them bare chested.

 

“Cas, are you  _ sure _ ? I’m messed up in a lot of ways, man, and-” Dean was cut off as Castiel came over to kiss him firmly, the hunter feeling tears in his eyes as he was blatantly accepted for several minutes, with deep kissing that made his hard dick weep in his pants. Cas was all muscle and tan skin, and just feeling his bare shoulders was driving Dean crazy, not helped by Cas’s hands running all over him. “Okay, yeah, okay, we’re doing this.”

 

“What have you done so far, with men? What are you comfortable with?” Castiel asked, his eyes staying on Dean as he walked over to shut his bedroom door, bending down to get his shoes and socks off quickly. Dean’s mind raced as the angel stared up at him from on his knees, then his mouth watered when he got up and started working on his dress pants. The hunter’s hands undid his belt haphazardly as they shook. “I have little experience, but since everything is new...I’m alright with most anything, Dean.”

 

“Cas, I’m so turned on right now, you could pull out a saddle and a pair of spurs and I’d let you ride me down the halls.” Dean said, yanking down his pants and boxers, only stumbling a little as he shook them off his foot, his cock bobbing with his movements. Castiel...moaned, when he saw all of him, and it made Dean so damn happy that Cas liked what he saw. 

 

“I think I would like to ride you, with or without the saddle. You’re a little bigger than I am, I hope that’s alright.” Castiel said, sliding down his pants more slowly, revealing the most beautiful cock Dean had ever seen. His own member was a little over eight inches, meaty and thick, and hung heavy. But if Dean’s was like a club, Castiel’s was like a sword, seven inches of straight steel that looked like it could shatter diamonds. Cas looked like a porn star, and Dean’s cock started to leak onto the floor. 

 

“Jesus, Cas, that’s a hell of a lot better than ‘alright’. Anything, Cas, anything you want. I’ve...I’m so mad at myself for waiting this long, for not-” Dean said, shaking his head, arousal and anger pulsing through him. Years, they could have been doing this for  _ years _ , if he had just pulled his head out of his ass. “You’ve been so patient with me. Your show. What do you want?”

 

“Well, there is one thing that my limited sexual experience hasn’t let me feel. Oral sex, or being on the receiving end at least. I very much want to give you pleasure, but...maybe it would be best if you showed me how?” Castiel asked, smirking a little as he stepped forward. Dean surprised the angel by lunging forward as well, and showed his angel just what his years of kissing all sorts of different women had given him. Cas was shoved back against the wall, overwhelmed by Dean’s tongue and lips and fingers and...he was everywhere, and Cas found himself whimpering and submitting to the taller man, who slowly started to sink down, kissing his angel’s body on the way. 

 

“Anything, Cas. Gonna make you feel so good.” Dean promised, smiling when Cas finally arched off the wall with a surprised noise when Dean licked and sucked at the sensitive area between his hips and groin. “Well, hello there. Tell me if you need me to stop, or if you want something, ‘kay?” he continued, Cas only able to nod for a few seconds before Dean’s mouth enveloped the head of his cock.

 

“ _ Dean _ .” Castiel groaned, the hunter trying to be slow, but desperate to take more of his friend’s cock inside his mouth. He gently played with Cas’s balls, carefully stroked his shaft, and slowly worked in inch after steel inch into his hot, wet mouth. The sounds that Cas was making were driving Dean insane, but he left his cock alone, knowing he’d blow right away if he started stroking himself. “That feels wonderful, I don’t...tell me if I need to do anything.”

 

“You don’t gotta do anything, just enjoy it.” Dean said, licking and sucking gently along the steel rod he was finally getting to enjoy, loving the cry Castiel let out when he started lapping at his balls. He thought about his past experiences with Crowley. “But, uh...if enjoying it means you need to grab onto me, or my hair or anything, and...fuck my face, you can do that too.”

 

“But wouldn’t that hurt you?” Cas asked, his eyes lidded and dark as pleasure radiated through his nether regions. He was actually having to concentrate on not finishing, despite his usual level of control; Dean was too hot, and too skilled, and Cas was fighting a losing battle. 

 

“Oh, no. Um...I actually enjoy it, kind of.” Dean tried sheepishly, gently pumping the angel’s dick and keeping his eyes glued to it for a moment. When he looked up, Castiel was weakly raising an eyebrow at his obvious attempt to hide something. “Alright, fine, I love it. Like, it goes right to my dick and makes me wanna bust kind of love it. It’s...Crowley was really rough with me, especially to start with, and somehow he  _ knew  _ I would like it. The bastard...but he was right, I kinda like it rough. Is that weird for you?” 

 

“Dean, I  _ like  _ the idea of being forceful, with you, but much of my enjoyment would come from yours. How forceful are you comfortable with?” Castiel asked, pushing himself a little off the wall and taking a more domineering stance over the Winchester, who’s eyes widened at the immediate acceptance and enjoyment of the idea, which the angel noticed with a smile. “I’ve commanded armies of heaven, Dean. Getting a human to obey and please me should be easy.”

 

“...this...yeah, this is the hottest thing I’ve ever experienced, right there.  _ God _ , Cas, I don’t know, a safeword wouldn’t even work here, since...fuck.” Dean tried, his cock throbbing and starting to ache. “As forceful as you want to be, I can take it. Whatever you want. I trust you.” he promised, Castiel rewarding him by bending down and giving him a deep and slow kiss that made him want to melt. Cas just stared at him for a moment, when it was over, their faces close.

 

 “What I want...is for you to keep sucking on my cock.” the angel of the lord said, rising up and staring down at the grateful human with steely eyes, guiding his head towards the hard rod and letting out a pleased hum as it slowly sunk into the other’s mouth. “I can monitor your oxygen levels, your heart rate, anything I need to make sure you’re safe. Which means you can choke...” Castiel said, pulling Dean’s face all the way to his crotch and feeling the man’s throat spasm around his dick, letting out a loud groan at the feeling. “...and stay here, while I enjoy it.”

 

Dean’s brain misfired and shot all possible blood in his body right to his cock, as he choked again on Castiel. His friend was choking him on his dick. He was holding him there, and letting out satisfied sounds, and running his fingers through his hair and talking dirty to him and throbbing inside of him and Dean was slowly starting to run out of air as he drooled and gagged and then he was gasping in a lungful of air. 

 

“You’re alright?” Cas immediately asked, a hand coming to cup his face and look into his eyes, stroking away the tears that had come when Dean had gagged. Dean could only breathe raggedly and stare up at Castiel in awe, who acquired the most lascivious smile the hunter had ever seen on a man. “You’re alright. Open up.” the angel ordered, and Dean let out what could only be called a whine as Cas’s perfect dick slid back into his gullet.

 

Dean would say he was in heaven, but he had been there, and this was better. This was so much fucking better. Castiel started out slow, pulling Dean’s head all the way to his pubes again and again, relishing the feeling of finally being inside the hunter, and every time Dean had to work on staving off his orgasm. Crowley had been amazing, but this was the angel he’d been pining after for a decade, and his dick definitely knew that. Slowly, Castiel grew bold, and began to thrust, letting out gentle moans at the feeling of Dean’s tongue and throat.

 

“So  _ good _ ; Dean, this is incredible. You’re so slick, and receptive...if I had known you liked this kind of treatment, I would have put you on your knees many years ago.” Castiel said, Dean’s entire body arching like it was hit by a live wire, his eyes pleading as the angel thrust forward and stopped, staying balls deep inside his throat and watching Dean spasm and choke before he released him. “You’re certain I’m not hurting you? I can go harder, if you think you can take it.”

 

“If you...if you go any harder, I’m going to cum all over myself without doing a thing.” Dean said, smiling deliriously up at Cas, who surprised him by lifting him up and pulling him into a heated, sweaty kiss. He groaned as he was led back to the bed, his angel kissing and licking at his neck as they moved. “Jesus, Cas, I didn’t expect you to be so into this, or so damn good at it.”

 

“I’ve long imagined what I could do with you, Dean. And I’m not  _ completely  _ inexperienced. Are you certain it can be ‘my show’? I want you to enjoy yourself.” Castiel asked with a frown, Dean just smiling at him and feeling only a little nervous when he put his arms around the angel’s strong back, promising himself he was going to examine every inch of this Adonis when he was slightly less desperate. 

 

“Cas, I’m really,  _ really  _ hoping we’re going to be doing this more than once. Like, all the time. You’ve been waiting a lot longer than I have, and only done this kind of thing a few times. Today, we do whatever you want to do. Alright?” Dean said, waiting until Castiel nodded before he leaned his forehead against his friend’s, the two of them taking a moment to enjoy the feel of their bodies gently pressed together.

 

“I would like to swallow you, Dean. To feel you finish inside me, to taste you.” Castiel admitted gently, Dean shuddering but not opening his eyes as he nodded. Cas gently pushed him back onto the bed, helping him move up until his head was on the pillows. Then, Dean opened his eyes, his mouth falling open when Cas started stroking his cock. “Tell me if I do anything wrong, I haven’t done this before. But I will be careful with my teeth.”

 

With that, Castiel took the head of his best friend’s cock into his mouth, and began to taste it with his tongue, causing Dean to groan and flex beneath him. A huge shot of pre from Dean’s very productive cock had the angel humming in satisfaction, the taste something he was eager to have more of. He gently jacked the other man off, not wanting him to finish too quickly, and continued to gently suck and taste the head, but Dean was getting close anyway.

 

“Cas, I’m getting close, haven’t cum in weeks!” Dean warned, and Castiel only took a second to think about it before he gripped his friend’s cock harder and started pumping him, sucking hard on the head and popping it repeatedly in and out of his mouth, Dean’s body starting to convulse as his orgasm was being worked out of him. “Cas,  _ fuck _ , here it comes!”

 

Cas had seen porn before, but Dean was outdoing all those porn studs with his massive rod and overfilled balls, his hunter screaming as every muscle in his body flexed and stretched as he unleashed his cum into Castiel’s waiting mouth. Supernatural creatures often had very huge loads, but a pent up Dean Winchester, the sex god, still filled up Castiel’s mouth almost faster than the angel could gulp it down, shocking the less experienced man. It took much longer than he thought for the human’s orgasm to slow, but he relished every drop he got, only stopping his sucking when Dean began to pull away and protest.

 

“Holy... _ shit _ , Cas. I needed that, so damn badly.” Dean said, practically melted into the sheets, smiling as Castiel climbed up on top of him, breathing hard himself. “Did you...was that OK? I’ve met a lot of girls who don’t like giving head, it’s alright if you don’t-”

 

Castiel slipped his cum covered tongue into Dean’s mouth, the hunter moaning at how slick and hot the angel’s mouth was now, more so than before. Castiel gently ground himself down against Dean, keeping the kiss slow and deep, leaking against Dean’s stomach to show him how arousing the experience had been for him. Dean got the message, and after a few minutes, flipped Cas over so the angel was underneath him.

 

“Can I return the favor, Cas? You can fuck a load into my throat if you want.” Dean offered, his grin only a little nervous. This was still so new, but so damn hot, and his cock was already starting to harden at the idea of swallowing Castiel’s load, of seeing him cum.

 

“That sounds wonderful, Dean, but...well, angels naturally produce a very large amount of semen, because of our grace. Normally I would be able to increase or decrease the amount, but I’m too...aroused. When I finish, it’s going to be quite excessive.” Castiel warned, but Dean surprised him with a small groan as he started to slide down towards his hard prize. “Dean?”

 

“Crowley too, Cas. He had to use some demonic mojo to keep from fucking drowning me. Can you do something like that?” Dean asked, making the angel gasp as he started jacking him off before he could answer, Castiel looking down at him uncertainly. “I  _ like  _ it, Cas, it’s fucking hot, like you fucking my face. If I can’t swallow all of it, I’ll just keep jacking you off, OK?”

 

“Too much talking.” Castiel complained, shocking Dean as he used both hands to shove the hunter’s head down and begin thrusting upwards. The sounds of protest from Dean’s body only edged Cas on more, knowing Dean actually loved the treatment. The angel moaned and began truly fucking the Dean’s throat, too amped up to hold back anymore. “I want to do this every day, just heal your throat whenever I need and keep using it like this, over and over and over...”

 

Dean’s cock was hard as rock again, throbbing as his face was used as a fuck toy by the sexiest man he knew. Cas knew what this was doing to him, he could see it in the angel’s eyes, and it just turned them both on more. Castiel’s mouth fell open, and he started closing his eyes and leaning back against the pillows, and Dean knew he was getting close to the edge. He took over then, and Castiel let him, the angel reaching behind his head to grasp at the pillows while Dean pumped and sucked his beautiful cock powerfully.

 

“Dean, don’t stop, I’m almost there...” Cas ordered, as if Dean had the slightest idea to the contrary. Dean used his other hand to start playing with the angel’s balls, and that surprise was the last straw for Castiel, who arched back silently and began to erupt into Dean’s hole. The hunter moaned as cum flooded his mouth, but quickly realized that Cas hadn’t been exaggerating, and had to struggle to keep swallowing down his seed. Instead of slowing down, Castiel just kept cumming more, his orgasm getting stronger and cries starting to leave him. Dean couldn’t keep up, and even though he swallowed more cum than he ever thought possible, Castiel’s whole body and bed were a mess of sticky white release by the time the angel finally relaxed into the bed. 

 

“Oh my god...” Dean said, his stomach making loud gurgling noises and his wrist and jaw aching from the longest orgasm he’d ever witnessed. He was lucky he hadn’t eaten breakfast yet, or there would have been no room; he felt full and...satisfied. “You weren’t kidding, man. You alright?”

 

“Very...very much alright. I couldn’t control myself at all, Dean, I’m sorry. That’s why I kept my hands to myself, I think I would have just held you down the whole time otherwise.” Castiel said, looking down at Dean like he still was considering doing just that, making the hunter lick his lips. “I’m going to need to ask Crowley how he kept you safe. I would like your throat around me the whole time I finish, if possible.”

 

“Maybe, uh...maybe he could show you if...you know, if you’d be interested in that kind of thing.” Dean offered, surprising himself. Crowley and Cas at him together...his cock gave a little bob where it was neglected between his legs. His face reddened a little when Castiel grinned at him, his blue eyes practically sparkling. 

 

“I would like that very much, Dean. Now, come up here. I want to see if I like you using my throat the same way I do yours.” Castiel ordered, and Dean obeyed his angel, sliding up his friend’s muscular body and groaning as he slid deep into his throat.

 

Oh yes, this would be happening all the time. 

**Notes for the Chapter:**

> I promise, Jack hasn't been forgotten. ;) Expect a lot of him in the next chapter.


	14. A Trip Down Below

**Summary for the Chapter:**

> Jack needs to get away for a bit, and Crowley seems like the perfect person to help him out...until Jack starts asking questions.

Poor Jack was in a bit of a hard situation, and the hard situation was his dick. He could hear Dean and Castiel making out just down the hall, and he knew that if everything worked out the way Castiel wanted it to, there would be a lot more going on very soon. His dick also knew that, and was forming a huge bulge in his jeans, which was both pleasant and distracting. Jack knew how to take care of it by himself now, but it was more the difficulty of not walking over there to have sex with the two men, especially given the time he and Castiel had just had.

 

Jack thought about it for some time, the situation only getting worse when the sounds of Dean taking Castiel into his mouth reached his supernaturally enhanced ears. He knew if he stayed he’d likely go knock on their door, or fly himself inside, or something else rash and unwise...so he flew himself elsewhere, thinking of the one other being that had offered to help him with such a situation.

 

Of course, arriving in the middle of hell without any warning might also have been unwise, Jack told himself, as a dozen demons armed with guns and angel blades surrounded him. He was pretty sure none of them could hurt him, but he didn’t think Crowley would appreciate him wiping out his guards either. The one upside was that his erection had disappeared.

 

“Who the hell is this kid?!” one of the guards yelled, but then another, a striking woman, lowered her pistol. She was a brunette with striking eyes, and she looked him up and down once more before speaking.

 

“Stand down, all of you. It’s Jack, the Nephilim. Most powerful being currently known on the planet? Don’t think those cattle prods would do much, if I’m remembering the files correctly.” she said in a gorgeous British accent, and all the demons slowly lowered or put away their weapons. The woman walked over, smiling brightly, and held out her hand, which Jack took. “Bela Talbot, pleasure to meet you. Lord Crowley’s talked a lot about you. Is he expecting you?”

 

“Oh, no, I just really wanted to see him. Is he busy? I tried to fly myself to him, but I must have done something wrong.” Jack explained, looking around. This place was...dark, smokey, and seemed endless. The ground under them felt like rough stone, and the only thing visible around them was a large red door that all these demons seemed to be guarding. Everything smelled funny, and not in a good way...he didn’t love the feel of this place, but Jack knew first impressions could be wrong. After all, upon their meeting, Dean shot at him.

 

“It’s probably the angel warding, especially around Crowley’s private chambers. I’m surprised you were able to get into hell so easily at all, let alone to his doorstep. You really must be powerful as they say. Come on, I’ll take you to him. I don’t imagine he’d refuse to see you.” Bela said, leading the way and opening the door for him. It led to a surprisingly normal looking hallway, albeit very fancily decorated. Jack could hear Crowley’s voice towards the end of it.

 

“...and perhaps relocating a few of our best towards the Middle East. I’m interested to see how our improved deals work over there.” Crowley said, and the two guests came up to an intricately carved wooden door, which Bela knocked on after only a few seconds of hesitation. The door opened, revealing the King of Hell in a luxurious looking silk robe. “I thought I told you morons-...Jack, well, this  _ is  _ a welcome surprise, if a little unexpected. Come in. Thank you for bringing him Miss Talbot, that will be all.” Crowley said quickly, shutting the door on an eager looking Bela, who audibly huffed before she went on her way. She had been hoping for a better in with Crowley, or at least a chance to see the King’s private quarters. 

 

The demon put a hand on the small of Jack’s back and led him into a beautiful bedroom with...sunlight coming through the windows? Jack didn’t think that was possible in hell, but there it was, just the same. There was a big, opulent desk against one wall, and numerous bookcases built into most of the rest, but the most obvious feature was the giant, bigger-than-king sized bed up against the left wall as he walked in. And the naked, muscular demon inside said bed, relaxing and reading a book. Antonio looked up at their guest, then at Crowley, silently seeing if he was alright to stay where he was, but Crowley just waved at him to indicate he was fine.

 

“Now, my young friend, what is it I can help you with?” Crowley asked excitedly, keeping his hand on the small of the boy’s back, abuzz with both arousal and alcohol. The Nephilim in his bedroom was more than he could have hoped for, whether for practical purposes or something more...private. Jack’s eyes wouldn’t leave Antonio’s biceps, so Crowley was certain getting Jack in the mood wouldn’t be difficult, if things went that way.

 

“I...well, Castiel and Dean...I’m not sure I should be talking about it.” Jack said distractedly, Antonio smirking and going back to his book, but putting his arm behind him in a rather seductive pose that had the young man swallowing audibly. “I didn’t mean to interrupt anything, I know this was unexpected.”

 

“You’re not interrupting, we’ve been fucking each other on and off for the whole day. I take one day a week that is purely for my own desires, to relieve stress, drink, relax, and have a gratuitous amount of sex.” Crowley informed him, making the poor Nephilim turn and stare into the demons eyes while both men’s members began to grow. They were close to one another, and poor Jack was already so riled up from earlier...and this was Crowley. Seduction was second nature to him. “Now why don’t you tell me why you showed up at my door, hmm?”

 

Jack was fairly certain the demon was a little tipsy, given what he had been seeing with his adoptive family recently. He had asked Castiel about what alcohol did to people, and knowing it lowered inhibitions made him feel a little bit better about opening up to the demon. He started out a little slow, but rushed to get everything out once he started, feeling like a weight was leaving him. 

 

“Dean and Castiel are having sex, and I couldn’t...I would have barged in on them if I had stayed, I just want them both so  _ much _ . I’ve never felt like this before, I feel like I’m going crazy! Even after Castiel and I did fun stuff yesterday, I still need more.” Jack explained, looking down at his own erection, widening his eyes when he saw Crowley’s robe tented outward nearly a foot.

 

“So they finally are sealing the deal, are they? That makes me very happy to hear, Jack. Almost as happy as hearing how horny it makes you. You see, they do the same thing to me, can you tell?” Crowley said, reaching down and squeezing his barely covered member, making Jack’s mouth drop open. Jack was a little bigger than Castiel, but that monster put everything he had seen in person and online to shame. “Now, what fun things have you done with Castiel?”

 

“We...we kiss, and get naked, and we...are we going to have sex?” Jack asked hopefully, Antonio closing his book and getting up, Jack’s entire body shaking as the rock hard latino man walked over to them, putting a hand over Crowley’s shoulder and watching the boy with interest. They were all very close to one another, the heat in the room rising, and Crowley raised his hand to the back of the Nephilim’s neck.

 

“That entirely depends on you, Jack. If you think you’re ready, Antonio and I can both have a wonderful time breaking you in. You know how much I would love to teach you all the ins and outs...and ins, and outs, over and over. I’m also alright if you would prefer it to just be us, but clearly Antonio would like to join in the fun.” Crowley said, reaching down and taking the man’s hard seven inches in his hand, making him groan softly in surprise. Neither’s eyes left Jack’s, who looked like he was thinking hard enough to have smoke coming out his ears. Reason warred with heat in his gut, and he forced himself to choose the former.

 

“I just...I need to be sure, one more time. Then I’ll trust you. Then you can do whatever you want to me.” Jack promised, looking apologetic as he put his hand on Crowley’s shoulder, near Antonio’s, and golden light filled the king of hell once again. “Are you keeping any dangerous secrets that I would want to know about? Or trying anything that could cause harm to me or my family?”

 

“We do currently have the vessel of your father locked up in my personal dungeon, given that he was trying to bring about Lucifer’s return from the grave.”

 

“...what?! Why...why wouldn’t you tell us about that?!” Jack demanded, floored, Antonio backing up quickly, his arousal gone as he debated what to do. Weapons wouldn’t work against the kid, he was too strong. 

 

“Because the Winchesters already had him, and lost him. I love those boys, I really do, but sometimes they’re dumber than a pile of brimstone. I didn’t trust them with this. I wanted to tell you, but we haven’t yet been able to get the information on how he wanted to bring back your father out of him yet, to my great shame.” Crowley said, trying his best to fight or manipulate what he was saying, but Jack was too powerful. 

 

“Where is he? Can you take me to him?” Jack asked, and Crowley just snapped his fingers, one of the bookcases opening. Jack stared at the new doorway for a minute, trying to calm himself down, and finally looked back at Crowley. “Is there anything else?”

 

“Nothing much I can think of that would interest you. The demons are performing well as hunters, and if all keeps going as I hope, none but the most unlucky humans should ever have to worry about monsters or hunting again.” Crowley said, trying and failing to keep the rest in. “Which will allow Dean to devote his full attention to being the good little manwhore I know he wants to be. Ideally, you, myself, Antonio, that stupid, sexy angel, and any other man that wants to will be able to get a piece of that fine ass.”

 

Jack stared at Crowley for a moment, arousal attempting to take hold of him again, but he forced himself to focus. He released Crowley, who shut his eyes and focused on keeping his anger and outrage inside, knowing getting mad would only make things worse. This was what happened when he drank and let his dick do the thinking. To his surprise, the Nephilim’s hand returned to his shoulder, and he stared at it.

 

“I’m sorry, I know that’s not...right, to do to you, but I had to be sure. I’llgo and try to talk with him, see what I can learn. Please stay here. And...and maybe after, we can...if you still want to.” Jack said, feeling a sudden sadness as he realized he might have blown his chance to experience sex for the first time. Crowley didn’t reply, just stared as the Son of Lucifer strode past him and Antonio into the secret room, neither attempting to stop the boy.

 

“Are you alright, my lord?” Antonio finally said after a minute of weighted silence. Crowley nodded, finally moving and beginning to pace, scratching at his beard as he did so. Antonio had never seen the king of hell so cowed, and he wasn’t sure how he felt about it. “Do you need me to do anything?”

 

“Other than keeping what you’ve just seen a secret, no. We wait.” Crowley said, Antonio nodding and looking around for a moment before putting on his pants. It took a while before more words were spoken. “He’s strong, Antonio, stronger than anyone I’ve ever seen. Few weapons would work on him, few powers could contend with him. This is one of the biggest reasons I’ve sided with the Winchesters: they have the strongest being on the planet as their adopted child. I’m not an idiot; however much I like him and find him desirable, that boy could cleanse hell of every demon inside it in a single day if he wished it. The Winchesters are already a powerful force to be reckoned with on their own, but Jack...”

 

“That’s why you’ve tried to get close to the boy? Many on our council have debated if you’re trying to groom him for the throne, or for some kind of puppet regime.” Antonio said, expecting anger from the king, but receiving none. Crowley just looked a little tired, and gave out a big sigh.

 

“What I’m  _ trying  _ to do is change with the times. I’m trying to keep hell from becoming what every neanderthal’s mind up above thinks of us, and then have to worry about an inevitable war with humanity. Or whatever else the powers that be decide should eradicate us. I’m not trying to make the boy my puppet, I’m trying to show him and his three idiot fathers that I’m not the boogeyman out to get them.” Crowley said with exasperation, pouring himself another drink from a bottle that was worth more than every hair product Sam Winchester had ever used. 

 

“I trust you, my lord. I wouldn’t be here if I didn’t. Just...” Antonio started, Crowley looking up at him and seeing a surprising amount of concern in the other’s face. Their relationship was mainly that of leader and follower, even with the sex involved, but the king of hell had a feeling his right hand was devoted for more than one reason. “...don’t bite off more than you can chew.”

 

“I think I crossed that road a long time ago, when I started thinking of the Winchesters and their various companions as anything more than annoyances to be removed.” Crowley said dryly, finishing his drink in one swallow and feeling a little more relaxed. He poured himself another drink, and one for his companion, handing it to him with a meaningful look. “But thank you.”

 

“Always, my lord.”

 

______________________________________________________________________________

  
  


Jack made his way down some quite medieval looking stone steps, the stone walls and low ceiling making him feel a little anxious, an unpleasant buzz going up and down his spine. It only took a few minutes to reach the bottom, and it was a much less pleasant room than the one he had come from. Stone walls dripping with what he hoped was water had chains hanging from many different places, as well as hooks. A few finely crafted but bloodstained wooden tables held various implements of torture, and there were three strong looking metal cells with various runes etched into the them against the far wall. 

 

“...this is new. Didn’t think he’d try to torture me with visions of my...what would I even call you, my son in law?” Nick said from inside the cell on the right, on his knees with chains connecting him to the wall, a dog’s water bowl his only companion. Jack stared at him for a brief moment, still having a hard time not seeing his father in the other’s face, but there was something noticeably different, missing, when he looked for it.

 

“I’m not a vision. I came to see Crowley, and he told me you were down here.” Jack said, his voice stern as he walked up to the cage, wondering if this was anything like the one that had housed his father for so many thousands of years. He stared at the man inside, who looked rather like he’d been the punching bag for most of the armies of hell, wearing only jeans and a white, bloodied shirt. “Why are you trying to bring my father back?”

 

“I told you before, I want to be his vessel again. I don’t care what he needs, what he uses me for, or if the world freezes over because of it. I. Want. Him. Back. Now drop the holograms and get back to beating the shit out of me, I know that’s what gets you off.” Nick said, his smug (and bruised) smirk disappearing when Jack’s face turned to one of rage, and his eyes flashed brilliant gold. 

 

“I am not a  _ vision! _ ” Jack shouted, blasting the cage door off its hinges and warping all the metal around him. Nick scrambled back what little he could from the angry Nephilim as the wall behind him cracked. Jack walked inside with purpose, coming to stand over his father’s vessel and looking down with eyes that left no doubt as to his legitimacy. “You will  _ not  _ try to resurrect my father again. He wants to hurt my family, wants to hurt me, wants to hurt the entire world, and I won’t allow that to happen.”

 

Nick stared up at the powerful young Nephilim with fear, tears filling up his eyes. Jack had been about to make him reveal how he wanted to resurrect Lucifer, but took a step back when the man started crying, his eyes losing their glow as he frowned. Nick just groveled and sobbed, looking more pathetic than Jack had ever seen anyone look. His father’s vessel looked up at him pleadingly.

 

“Y-you don’t understand, I  _ need  _ him. I can’t live without him, I need to devote myself to his every wish, his desire. You can bring him back, can’t you? You brought back Castiel, you can bring back anyone.” Nick said, Jack shaking his head and frowning further when the man grasped at the bottom of his pants, clinging desperately, his chains barely letting him reach that far. “Please, I’ll do anything, anything you want!”

 

“There’s nothing you could give me that would get me to bring him back.” Jack said, his pent up frustration at everything the past few days had given him leaking into his voice. Nick was still for a moment, then slowly slid his hands a little higher, to the young man’s thighs, making goosebumps rise all over Jack. The young man’s body was so sensitive to touch, just that alone felt very pleasant. “What are you doing?”

 

“If I’ll never see him again, then I need someone else to devote myself to. And you’re the closest thing I’ll ever get to Lucifer. I want to worship you, to please you...let me show you how good I can be for you.” Nick offered, his face now devoid of tears, his hands sliding up further and stroking over Jack’s clothed bulge, causing a gasp to come out of the surprised Nephilim as his dick began to rise. “You haven’t had this yet, have you? Let me give this to you, let me show you...”

 

Jack had been pushed too far to resist. First Castiel, then Crowley...he was desperate, his angelic grace fueling his human arousal like a fan to the flame. No one in his family had realized what a hard fight he’d been slowly losing, and now there was opportunity in front of him. His belt was undone, and soon his pants and underwear were pulled over his aching member, Nick’s eyes widening at the large erection.

 

“Holy shit, kid. You’re as big as I am, easily.” Nick said, Jack moaning when a hand grabbed hold of his cock and began to slowly pump him, the vessel of Lucifer smirking at how easy this was going to be. He hadn’t sucked a guy off since high school, and never anyone quite this big, but like riding a bike...he swallowed half of Jack’s shaft in one go, pulling Jack closer so he had more slack from his chains. Despite himself, he was liking the young man’s approving moans as he got his cock wet, and soon was hardening in his jeans. He slid his hands up the Nephilim’s stomach and chest, playing with his nipples.

 

“We can’t, this is... _ oh! _ ” Jack cried as Nick swallowed his newly slickened member nearly down to the base, humming in approval at the forgotten feeling of a full throat, then gagging when Jack put a hand on the back of his head and pushed even deeper. Nick got off and coughed a few times, the years having left him rusty.

 

“Easy, we can-” Nick tried, but was cut off by a desperate cock shoving it’s way back into his throat, and the man gagged and sputtered as the strongest being on the planet began to take his pleasure from his mouth. Jack’s eyes were unfocused, his mouth open and slack as the urge to breed and fuck made itself unbearable. He slowly began to thrust, ignoring the sounds of Nick gagging, never taking his cock more than halfway out before putting it roughly back where it belonged.

 

“Oh god, oh god this feels so good, I can’t...I can’t stop, I’m sorry...” Jack said weakly as the reasonable part of his mind finally gave up, the young stud finally giving in and beginning to fuck in earnest. Nick’s poor throat was forced open again and again on Jack’s hung cock, his hands uselessly trying to push at the Nephilim’s thighs to slow him down, while both of Jack’s were gripping his head firmly while it was used as a fleshlight. 

 

Only able to get the tiniest breaths of air between longer thrusts, Nick could only do his best to make Jack cum, using his tongue as best he could to stimulate the rod inside him. Jack just kept moaning and stuffing Nick’s red face full, in his own world of bliss that kept getting better and better as he felt his orgasm start to approach. Nick had never had sex with Lucifer inside him, so he was unaware of what was coming, only relieved when he began to taste the beginnings of Jack’s release. He was not relieved for long. 

 

Spunk  _ poured  _ into Nick’s waiting gullet as Jack howled with his orgasm, shoving his cock as deep as it could go and holding it there as the human fucktoy receiving it struggled. Some magic in the room was meant to keep those being tortured alive, and Nick was pretty sure that’s the only reason that he survived with no air for over a minute as more than a gallon of cum was pumped into his stomach, slowly pushing the organ to its limits and making his shirt stretch tightly against his belly. It took time, but Jack’s orgasm slowed to a stop, the Nephilim finally releasing his father’s vessel. Nick forced himself to swallow the final mouthful, then began to raggedly breathe. 

 

“Oh...oh...I’m sorry, I...it felt so...so amazing...I shouldn’t have...are you alright...?” Jack said, weak at the knees as he tried to feebly get his pants back up, feeling ashamed and light headed. Nick could only gasp in breath after breath, Jack slowly backing away as he zipped up his pants. What had he done? “I shouldn’t have come down here, I...” Unsure of what to do as guilt washed over him, Jack vanished, leaving a recovering Nick to regain his breath and composure.

 

Slowly, Nick rose to his feet, full and unsteady. But the smile on his face was a mile long.

 

“Thanks for leaving the door open...geez, that kid can bust one out.” Nick complained as he rubbed his aching stomach. It wouldn’t be full long, he reminded himself, and struggled with his chains for only a moment before the warped metal gave way, the other even easier. He moved quickly, unsure of how long he would have, grabbing his water bowl and heading over to the cabinets on the other side of the room as he stripped off his shirt, going for the salt used to torture naughty demons and making a ring around himself. “Almost, almost there...”

 

Making himself puke semon was not something Nick would ever thought he would do in his lifetime, but neither had been murder. He stopped once his shirt was soaked, and thanked Lucifer that burning was a form of torture, finding several books of matches. He allowed himself one deep breath, and a silent prayer to his master, before dropping the lit one inside and starting to chant.

  
“ _...qui dormiunt, ad dominum formosum...” _

**Notes for the Chapter:**

> Sorry this took a while, sometimes it's hard to find inspiration. Apologies if this isn't some people's cup of tea, I'm going where the story takes me, and things can't all be happy all the time...at least, not yet. I'ts Supernatural, people!
> 
> Also, I don't have a beta reader or anything like that, and often I'm eager to post when I'm done writing, so apologies if there are any errors or typos!


	15. Family Reunion?

**Summary for the Chapter:**

> Castiel and Dean are enjoying themselves...but something always comes up, doesn't it? Jack learns to take responsibility for his actions.

**Notes for the Chapter:**

> I'm so sorry this took so long and is kinda short. Stuff's been going on lately that made writing difficult, like breaking things off with the straight friend you're in love with! (can you guess where some of my inspiration comes from?) And having my appendix removed! So fun!

Dean’s breathing had finally gone back down to normal, after more than an hour of swapping head with Castiel, and another two orgasms wrung out of both of them. The angel had quickly learned how to deepthroat, and with no gag reflex, that meant a lot of sweaty abuse from Dean’s cock. He had never had someone so durable and willing, and after about half a dozen times checking that Cas wasn’t uncomfortable or hurt, Dean was ecstatic to learn he could essentially use his angel’s throat as hard as he wanted for as long as he wanted. He could hammer it in balls deep and stare down at the lust filled blue eyes staring up at him without worry.

 

Of course, Cas wasn’t one to miss out on getting his own dick wet, and sixty-nining was quickly introduced, messy and new and freaking incredible. Castiel still had to hold back some, but Dean was eager and knew enough to take his friend’s cock without the other needing to treat him like fine china. They spent ages exploring each others bodies, stroking and touching and pausing frequently to kiss each other breathless. 

 

Things had come to a head with Castiel on his back, repeatedly gulping up onto Dean’s dick, while the hunter languidly jerked and sucked Cas from above, relishing in the slick hole that he could just fuck into whenever he felt like. This, however, was not giving Castiel the stimulation he needed, and one of the angel’s gorgeous legs came up to loop over the back of Dean’s neck, shoving the man down onto his neglected cock and forcing him to go balls deep and stay there. The poor hunter gagged and struggled, but his cock was suddenly being jerked quickly and firmly, Cas’s mouth sucking hard on the head, and he could only moan as he began to get his throat used by his angel. 

 

“That’s it, Dean, all the way in. Your throat feels so good, I need to fill it up again. Smaller load this time, I promise. I’ll wait until you start your orgasm.” Castiel said, very matter of factly, only his small moans and heavy breathing proving how much he liked this. He was much quieter in general than Dean, who couldn’t stop gagging and moaning like a whore on the hard angel cock thrusting in and out of his mouth, especially when Castiel’s other hand came up and began playing with his ass, fingers creeping towards his hole. 

 

Feeling his orgasm starting to build, Dean found himself unable to do much besides get his head shoved repeatedly down onto his best friend’s hard cock. Everything was overwhelming, the heat, the sounds, even the smell of sex in the air, and Castiel’s fingers pressing hard against his hole felt like a bolt of lightning going right to his cock. It all became too much, and Dean screamed soundlessly as he began to fill his friend’s mouth for the third time, his eyes widening as Cas started shooting his own larger load into him. 

 

It took a little while to recover, but soon they were both almost breathing evenly with their heads on the same pillow, sweaty and extremely satisfied. Dean more so than his angel, who seemed insatiable, his cock still standing at attention despite the time spent emptying into the hunter’s belly. Dean felt full and exhausted, but better than he had since he could remember, and he slowly turned on his side to gaze at Cas a little uncertainly. His angel just gave him an easy smile. 

 

“That was...even better than I anticipated. Did I perform alright?” Castiel said, his knowing smile implying he knew he had, and Dean couldn’t help but kiss him again, slowly. The sexual energy was lessened, something deeper and heavier that he wasn’t ready to fully put into words leaving Dean’s lips, calling to something in Castiel and having him responding in kind. Long minutes passed, gentle touches and exploration from both of them so long overdue finally being given and taken. Finally, breathless again, Dean pulled away from Cas. “I’ll take that as a yes.”

 

“I am so, so sorry, for making you wait so long. I was kinda an idiot about all this.” Dean said softly, touching Cas’s face like he was afraid he wouldn’t get to again. The angel just grasped his hand and held it to his chest, smiling and resting his forehead against Dean’s.

 

“The fault doesn’t all lie with you. I should have spoken up sooner, maybe pushed a bit. Or at least wore something other than my suit and coat...you seemed to like that.” Castiel said with a small smirk, Dean reddening at the thought of Cas in a shirt and tight shorts. The angel ran his thumb over the hunter’s mouth. “But for what it’s worth, I think these lips have earned my forgiveness.”

 

“Yeah? Jesus, you’re still ready to go.” Dean said with a small groan as Castiel ground his erection lightly against him, grinning when Cas kissed at his neck and slid his muscled arms around his back. “Not that this doesn’t feel amazing, but I’m not as young as I used to be, Cas. Think I need a little time before round four. Guess we’ll need to experiment with how many you can go for, huh?”

 

“I don’t think you would remain conscious for that kind of experiment, Dean. Not to insult your sexual prowess, but angels can go for much,  _ much  _ longer than humans. Days, if desired.” Castiel said, ceasing his ministrations and leaning back, attempting to reign himself in. Which was difficult, given the awestruck expression on Dean’s face. 

 

“Days? I mean, I’m good, but I don’t think I’m  _ that  _ good. I’m, uh...down to try, though. Maybe after drinking a lot of water, or coffee, or one of those crappy smoothies Sam makes.” Dean offered, making Cas chuckle under his breath, Dean relishing the sound. This...just lying here with his angel, was as good as all the sex with all the women he’d ever had. He scooted closer, sliding a hand over Castiel’s stomach and playing with the flat plain of muscle. “Anything you wanna try Cas...I’m down. Like I said, your show.”

 

“Everything. I want to try everything with you, Dean. But I want to enjoy this, to enjoy being with you. I’m not in a rush, and I’m alright to go at whatever pace makes you comfortable.” Castiel said, sliding his fingers through his friend’s hair and enjoying the relaxed expression that appeared on his face. “And I don’t want it to always be ‘my show’, I want us both to enjoy ourselves. So if there are things you wish to try...”

 

“Oh there are,  _ believe  _ me. But-” Dean said, seeing a change come over Cas’s face. “What? Did I say something funny?”

 

“Jack is longing for me, very strongly. I can feel it, when a human longs for me. He’s probably been hearing us have-” Castiel said, his expression going from amused, to blank. “...something’s wrong. He needs help.” the angel continued, shoving a surprised Dean away as he leapt up and off the bed, flinging open the door and running into the hall, the hunter only a few seconds behind. Neither man cared about nudity with their adoptive son’s safety on the line, and Cas flung open the door to Jack’s room to reveal the Nephilim writhing on the floor.

 

“Jack! Hey, kid, you alright?” Dean said, kneeling naked by the boy and checking him over for injuries, but there didn’t seem to be any. Jack was clutching at his groin and stomach, hissing, his face red with pain and shame. “Come on, gotta tell us what’s wrong or we can’t help.”

 

“I did something bad, I...I can feel the spell he’s using, he’s trying to bring my father back.” Jack explained, looking up at the two of them with pain and regret in his eyes. “It’s my fault, I was just so...I couldn’t stop myself. But I can stop him, I just need to focus.” 

 

“Jack, what the hell are you talking about? Who? Who’s trying to bring Lucifer back? And how’s that even possible?” Dean asked, thoroughly freaked out. Jack’s eyes kept flickering gold, but then he seemed to lose his focus and wince again. Cas grabbed the hunter’s shoulder to get his attention, but it was hard for Dean not to think about how much he liked seeing the angel naked, even with danger at hand. 

 

“Angel blades, holy oil. And something to make sigils with. I’ll help Jack focus, you get supplies and...pants. Mine too.” Castiel ordered, and Dean felt relief wash over him. Things he could do to help, ordered by a hot naked guy. He could get used to that, he thought, running out of the room at top streaking speed. Cas turned back to help Jack, but the Nephilim was already standing, eyes finally shining strong as he shook off the distractions.

 

“No. I’m not putting you or anyone else in danger, ever again. I’m fixing this, and I’m doing it by myself.” Jack said, vanishing before the angel could respond. Castiel just...stared, feeling utterly helpless without his wings, feeling the ache of their flightlessness like never before. Jack was the closest thing he had to a son, and he couldn’t protect him...he couldn’t move for several minutes, even when Dean rushed back in with supplies and pants.

 

“W...where’s the kid?” Dean asked, looking around frantically, Castiel looking back at him with a lost expression.

 

“I have no idea.”

 

______________________________________________________________________________

  
  


It hadn’t taken Lucifer very long to make his way out of hell. The wards in Crowley’s chamber had given the slimey demon and his half naked boytoy enough time to escape, but didn’t stop the archangel from turning every bit of the expensive wood in the bedroom to splinters. It wasn’t much, but it would have to suffice until he could get his hands on the demon and have a little fun with him. Very painful, deadly pun. 

 

For now, he was walking along a random street in Kansas, making his way to the Winchester’s bunker and planning on just how he was going to pay all of them back for killing him. He couldn’t sense Michael in this world anymore, so he was pretty sure his brother had been trapped or taken care of. He was still trying to sort through Nick’s memories, but the man was so elated to have him back inside him it was hard to think straight. Not that he could blame the human...and he  _ had  _ done well in getting him back to the land of the living. Maybe he had underestimated Nick, and his devotion. With Michael out of the way, there was no one with enough strength on the planet to-

 

“Father.”

 

Lucifer stopped and smiled, shaking his head, and turned to look at his boy. The few humans who were on the street were scurrying away, and who could blame them? The anger and power radiating off the boy was powerful, and even if they couldn’t see his glowing gold eyes, their subconscious minds knew something dangerous was going down. The last Lucifer had seen, his boy had lost all his power, but apparently things had changed. Unfortunate. 

 

“Well, speak of the Devil’s brat. Look who’s got their mojo back. How many angels did you have to suck dry to get that glow back, huh? Last I checked, there weren’t too many left upstairs.” Lucifer asked, smirking. It hadn’t been that long since he’d been killed, and he was hoping his baby boy was still regaining his strength, given how long it could take for a Nephilim’s grace to recharge. “Hope you didn’t empty out the whole pantry, but I get if you have some impulse control issues. Like father, like son, am I r-” 

 

Lucifer was flung into the alley by a powerful wave of force as Jack stepped forwards, thudding against the concrete hard enough to make it crack. So that was a no to the needing to regain some grace theory. His boy felt even stronger than before, and he would honestly be a little proud, if it wasn’t for the murderous look in his son’s eyes. Well, he was kinda proud about that too, but less so when it was directed at him.

 

“I didn’t need to kill any angels, just a demon. He didn’t seem to mind. But I did help get rid of Michael, and that was without my grace. Now that I have it? I’m stronger than you.” Jack claimed, and as much as Lucifer wanted to try to argue, he could feel the pressure in the air as he righted himself. He had only felt this kind of strength from his father, and it made him more nervous than he cared to admit. But he just smiled, cracking his neck and flexing his wings a little as he hurriedly searched through Nick’s memories about anything related to Jack, hoping for something to help him.

 

“You could be, but do you really want to put that to the test, especially with all these humans around? I don’t know if you know this, sonny-boy, but archangel fights can get...messy. You wouldn’t want to have us slaughter any of these innocent people, would you?” Lucifer asked, seeing the slight hesitation on his son’s face, and grinning when some interesting memories surfaced. “Besides, I hear you have a real thing for this body I’m inside of. It would be a shame to damage the first mouth you’ve ever-”

 

There was a flash of light, and they were somewhere else. A very familiar, unsettling somewhere else. The spot where Lucifer had finally perished at the hands of the Winchesters. He stood upon the marks of his own burned out wings, while Jack stood in the same spot that Dean had appeared in, and Lucifer backed away a few steps in surprise, breaking out in goosebumps. It was daytime, but the light made his son no less intimidating, one hand clutched and ready to fight.

 

“I thought this place would be fitting, since I’m sure we both remember what happened last time. You...you  _ watched _ , as I stabbed myself. You tried to kill my family and friends, and used all of your power against them.. And then...you died.” Jack said, walking towards him, Lucifer’s blood running even colder than it usually did as he realized what was happening but was too shocked to fight it. His kid, naive little Jack Kline, was attacking him with fear and guilt. And it was working.

 

“I...that was wrong, I shouldn’t have...I was so  _ angry _ , why don’t you get that? We could have had everything, Jack, you and me! Maybe I acted rashly, but you betrayed me first!” Lucifer inisted, his words sounding empty in his own ears as Jack rushed at him, unable to stop the boy as he slammed him against the wall, shattering the few windows left intact in the building. He tried to push back, to fight, and his efforts were useless. “We can still have everything, we can still be a family!”

 

For the barest second, Jack looked like he wanted that. He was a kid without either of his birth parents, even if he had the world’s most caring and mishmashed family around him to raise him. He would always want his father’s love and approval, even if he wished he didn’t. Then his look was overcome by fury, and Lucifer knew he was going to die in the same church, and be mourned by no one.

 

“Why do you keep lying to me?! Why do you have to keep trying to kill the people I care about?! Why can’t you just...why can’t you just  **_stop hurting people?!_ ** ” Jack cried, his power flowing into his father as his hands connected with his shoulders, tears appearing in his golden eyes as Lucifer cried out. The archangel could feel grace digging itself deep into him, inescapable and unstoppable as it brushed past any and all of his defences. 

 

Time passed, though how much, neither being could say. Some time later, Jack just...let go, letting Lucifer drop to his knees in exhaustion. The Nephilim just let the tears fall as he beat himself up inwardly, unable to work up the strength to do what he knew was the right thing, but...this was his father, and Jack knew a small part of him, however tiny, cared about him. 

 

“Can’t...can’t off your old man, huh?” Lucifer said weakly, getting up slowly and falling back over once as he did so. He felt like he had been hit with a thousand lightning bolts, and not in a fun way. He stared at Jack, who couldn’t look at him, and tried to come up with something snide, or mocking. “I don’t...I don’t know what to say.” he finally uttered, feeling a little like how Jack looked. Broken and sad.

 

“Just...go. And if you try  _ anything  _ to hurt my family, or the innocent, I’ll come for you, and I’ll stop you.” Jack said, finally looking up. And through the tears and the pain on his face, was something that shook Lucifer, because it hadn’t come from him. It didn’t even come from Jack’s mother. It came from the Winchesters, and something deep in the Devil’s gut knew that ‘stop’ would mean forever, no coming back. Lucifer flew away as fast as his wings would take him, and he didn’t slow down until there was an ocean between him and his terrifying son.

 

______________________________________________________________________________

**Notes for the Chapter:**

> I'll try to write more this week, let me know if there's anything you guys ever would like clarification or more detail on!


	16. Devil's back...now what?

**Summary for the Chapter:**

> Everyone's scrambling...but hopeful.

**Notes for the Chapter:**

> The last chapter felt too short, so I sort of updated again pretty quick. The upside of recovering from surgery: Time to write!

Many people across many different globes have tried throughout history to get the attention of their creator. Grand crusades, heartfelt prayer, human sacrifices, burnt offerings, you name it. Given that God was a bit picky with what he paid attention to, rather like a bored person attempting to find something to hold their interest on television at 3am, very few of these grand gestures actually worked to get his attention.

 

However, there weren’t many worlds where he had grandchildren, and even fewer where those grandchildren bested their parents in battle, and that was enough to give Chuck reason to take a gander at what was happening in one of his favorite dimensions. What he saw was something slightly distressing to the author: His story had gone off-script. This was both disturbing, and greatly interesting, for his writing was impeccable, and few things were ever able to derail it.

 

So, Chuck left the space in which he observed all his different dimensions, when he wasn’t enjoying any of them from within, journeying to see what had changed. And as he did so, a mysterious Someone popped over into this same space, quite sneakily. Taking care to not touch or disturb anything, this Someone made their way through the space outside of all other spaces, until he came to a Door. Normally locked, the Someone summoned a key to quickly get through the door, relocking it behind him and hoping his presence would go unnoticed.

 

This Someone walked through the Empty, normally inaccessible to his kind, and was unsurprised to find the door gone when he turned around. So on he walked, his slippers making as little noise as possible, his breathing even and quiet. It was hard to tell time in this place, but perhaps only ten minutes or so had passed when he finally knelt down and gently knocked at the floor. Soon, a pool of black goo was forming in front of him, and this Someone attempted to stay calm as he brought out a small whiteboard and a dry erase marker, finishing writing out his message just as the Shadow finished assuming the form of the man in front of him. Shadow and Someone sized each other up for a moment, before the Someone turned around his sign to reveal his message.

 

_ I have a proposition.  _

 

______________________________________________________________________________

  
  


When Jack finally returned to the bunker, his eyes full of tears, he explained to his two dads what had happened to cause this whole debacle. Dean wisely stayed silent as he paced around the room, Castiel doing his best to calm the boy and assure him that everything was going to be alright. Dean knew in the past he had reacted very badly when people he loved did things like this, lashing out in anger at Sam, Cas, and others because of his own fear, and he was doing his best to change that behavior.

 

“Do you hate me?” Jack finally asked from the bed, where Castiel had an arm across his shoulder in a comforting embrace. Both he and Dean had acquired clothes and other supplies, ready to fight or travel once they had some idea where Jack had gone. The Nephilim looked so broken and ashamed, Dean felt his heart give a lurch, and he reminded himself that he was partially responsible. If him and Cas hadn’t been bumping uglies, or if he had helped Jack out with sex questions, maybe this wouldn’t have happened. 

 

“No, no Jack. I’m not angry at you, I’m just...angry. I thought this was over, I thought...I thought we beat him, for good. But are you sure that whatever you did, it might have him weak?” Dean asked hopefully, wondering if they’d be able to take down the Devil again without an archangel. They had Jack, but asking the kid to kill his own father...that was a tall order, even when it was Lucifer.

 

“Not weakened, exactly. I gave him an...order, I guess, and it felt like when I made him tell me the truth. I burned it deeper inside him; I didn’t really know what I was doing, but...I think it will stop him from hurting anyone, at least for a while.” Jack said uncertainly. He had no way of knowing exactly what he did, and neither did anyone else, he was too unique. So he had to go with his gut, and that’s what his gut told him. 

 

“Well, that’s something at least. I’m gonna call Sam, mom, and Bobby, let them know what’s going on.” Dean said, grabbing his phone and nodding as Cas as he went towards the door, pausing briefly before leaving. “And kid? Glad you’re alright.” he added, and Jack gave a little smile as Dean walked out, letting out a breath he felt like he’d been holding. He looked guiltily over at Castiel, wiping his hands on his pants a bit and trying to find what he wanted to say.  

 

“I’m sorry I didn’t just wait, or find something else to do, I just...hearing you and Dean, it was so hard not to just walk over and-” Jack started, surprised when Cas gently kissed him, slowly helping Jack relax into it with his hands rubbing his back and shoulders. The angel waited to stop until the other man’s heartbeat had slowed down and steadied, and he pulled back to brush some hair off Jack’s forehead. 

 

“Jack, my first time was with a reaper who killed me afterwards. I’m not going to judge you. Sex is...messy, and not always perfect. Sometimes there are regrets, or mistakes made. That doesn’t mean there won’t be amazing times in the future, or other times with regrets. That’s part of life.” Castiel said, Jack slowly nodding before burying his face in the angel’s shoulder and sighing deeply. “We will deal with Lucifer, and whatever else comes our way, together.”

 

______________________________________________________________________________

  
  


“Yeah, that might be best for now. Just make sure you’ve got a shit ton of angel warding up, I’ll see if Jack can get you guys some extra holy oil too. Let us know if you hear anything. Yeah, love you both. Bye.” Dean said, hanging up on Bobby and his mom, who thought it would be better to stay at Bobby’s house in case something happened closer to their neck of the woods. They both knew to pray to Cas or Jack if anything happened, and he breathed out a stressed lungful of air while he stared at his phone...he had already called Sam, who was on his way back, but...he dialed in three digits and brought the phone back up to his ear, waiting.

 

“Well, if it isn’t the illustrious Dean Winchester, taking time out of his busy schedule to call the common folk.” Crowley said, sounding frustrated. Dean could understand, since he was one of the only ones who hated Lucifer as much as he and his brother did. Not to mention how long it had been since he had talked with Crowley, especially since they’d had a sort of...arrangement. He leaned against the kitchen counter, weighing his response for a moment.

 

“You’re alright? Not hurt?” Dean finally asked, and the silence on the other end of the phone was deafening, before a very stressed sigh was heard on the other end.

 

“Yes, we’re alright. The warding lasted long enough for Antonio and I to get us and our guard out. But Hell is scrambling like a kicked anthill, it’s all I can do to keep my less loyal demons from rioting. Is the boy alright? I sensed him leaving, so I assume he’s with you.” Crowley said, sounding a little worn down. Jack had told them what he had done to Crowley, and how bad he felt about it.

 

“Yeah, he’s shaken up pretty bad, but he...they fought, sort of, and he thinks he managed to do something to Lucifer that might make him easier to handle. We’re not positive how well it worked, but we’re trying to be optimistic over here. Either way, Lucifer ran, so maybe that’ll help you keep your troops in order.” Dean explained, glad to hear Crowley’s small chuckle on the other end of the line. “He’s...he feels pretty bad about what happened, even before Lucifer.”

 

“That does warm the cockles. He’s a good kid, even if I’m a bit peeved at him. Tell him I expect a very carnal form of repayment, hopefully sometime soon. Speaking of carnal...I hear there are some developments on that front with you and your little angelic soldier. Will I hear wedding bells in the future?” Crowley teased, Dean shutting his eyes and feeling his jaw clench. He was going to have to have a talk with Jack about what was alright to talk to slimey demons about.

 

“You know this call was just so I could make sure Lucifer hadn’t ganked your ass, right?” Dean tried, but there was smug silence on the other end. “Alright, fine, yes, Cas and I...fooled around, are you happy? You were right, I was wrong, and my whole damn family knows I like dick.” Dean admitted, hearing Crowley’s approving hum on the other end of the phone.

 

“And about you and I? I do believe that was part of the deal, was it not?”

 

“Oh come on, Crowley. I told Sam, and he laughed his ass off, that’s all you’re getting.”

 

“I suppose I could consider that suitable enough payment....if...”

 

“If?”

 

“I don’t suppose this new ‘development’ with Castiel allows for any sort of flexibility? I would hate to find out I had given up such a delightful lay simply to win a bet. And it has been quite some time since you and I have had any sort of...dalliance.” Crowley said, sounding casual, and Dean stared at his feet for a moment. His pride was warring with his excitement for all of this new stuff, which was only somewhat dampened by Lucifer coming back.

 

“...alright, Cas...we mainly just...swapped head, and made out a lot. And it was  _ awesome _ . But...we talked about you, maybe, showing him some...stuff?” Dean said quietly, double checking there was no one around. He had been thoroughly satisfied earlier, but the adrenaline of everything had him going a little again, and he had to work to keep his boner from getting out of control. “Like that thing you do to keep my lungs clear, or...you know, anal? Cas seems pretty open.”

 

“Mr. Winchester, you have most assuredly improved the quality of my day tenfold. I’ll make you a deal: Let’s both do whatever we have to do to prepare for whatever problems could arise on account of God’s brattiest son, and then the three of us will have a little get together. One rule: I want to be there the first time he gets inside you. Seeing you split open on his cock is nearly as desirable as getting you on mine, which will likely be happening soon after.” Crowley promised, and Dean lost the battle with his erection.

 

“Yeah...yeah, sounds good. So, uh...lemme know, I guess, anything about Lucifer or...or that.” Dean said lamely, wondering if he’d eventually stop being so awkward about this kind of thing. “I don’t know how much more prepared we’re gonna be able to get over here, since fighting archangels seems to just be a regular Tuesday for us.”

 

“Point taken. In that case, do what you can, have fun with your pretty little angel, maybe give Jack a lesson or two in ‘bumping uglies’ if you have the time, and I’ll let you know when I’ve gotten Hell back under control. I’m excited to see you again.” Crowley said genuinely, and Dean felt himself blushing. It was different, being friendly and open with the king of hell. Not bad, just took some getting used to.

 

“Yeah, alright, don’t get sappy on me. Let us know if you need us to stab any demons that get outta line.” Dean said, and Crowley just chuckled again before hanging up. Dean smiled, more hopeful than he had any right to be. But they had Jack, and the king of hell, and their whole family ready to take down the Devil. Better odds than what they’d had before. Maybe the dickbag would stay in whatever place he’d hidden himself away in this time.

 

______________________________________________________________________________

  
  


Lucifer watched the bunker from where he stood across the street, hands in his pockets. He knew he could probably force his way in pretty easily, probably take out the Winchesters and their insufferable pet angel before Jack could stop him. But his son had let him go, even if he had threatened him, and for the first time...Lucifer didn’t know what to do. He felt the pricklings of guilt inside him, however small, and he wanted them to go away.

 

Lucifer had been the one to betray Jack last time, if he was really being honest with himself. And hadn’t that been what his father had done to him? Hadn’t that been what had given him all this anger, and rage, and resentment, and he had turned around and done the same thing to his own son? He was having a hard time justifying it in his mind like he usually could; he just couldn’t get the image of Jack’s tears out of his brain, and it was making him squirm. 

 

“Trouble with your conscience, brother?” Gabriel said from beside him, chewing on something sugary, Lucifer not even bothering to look over. He shouldn’t be surprised, all things considered. Gabriel always found a way back, though how he got himself out of this one was beyond him. He’d been looking for any tricks this time, so he was pretty sure his brother had actually died. 

 

“Just when I thought I was done with the family bonding time. I guess out of the four of us, you would have the least to feel guilty about, huh? You already gave me quite the talking to last time, Gabe. I’m good with the Righteous Advice.” Lucifer insisted, but didn’t remove the hand his brother placed on his shoulder.

 

“Come on, let’s talk. Little Jack will still be there after you’ve had a chance to hear me out. I know a pretty good Italian place we can go to.” Gabriel offered, and Lucifer let himself be led down the street.

 

“Yeah? Close?”

 

“Italy.”

 

And they disappeared in a rush of wings. 


	17. Not Working Out a Safe Word

**Summary for the Chapter:**

> When research fails, pizza seems like the best solution! But they've got time before Sammy gets back with the food...

Dean couldn’t stop thinking about dick.

 

This was a little bit of a problem, given the situation they were currently dealing with, but it was like a dam had broken in his mind, and he couldn’t stop the images and fantasies from escaping. Cas and him had finally gotten together, and every time he let his thoughts wander the tiniest amount, he would imagine the angel’s beautiful chest, or the feel of his hands, or the sound of his rough breathing...or his perfect cock, and how it felt deep in his throat. 

 

Whenever he tried to think of anyone other than Cas, the problem remained. Crowley’s words had put thoughts of the demon and Jack in his mind too, and how much he would like them each separately...or all together. Every fantasy he’d tried to keep down all his life, every urge he’d suppressed, they were all out now. Maybe if Sam hadn’t been there, he would feel more alright to delve into them a little, but even though his brother was clearly accepting (and maybe bisexual?), he still felt a little voice of shame inside his head whenever he thought about men.

 

Currently in the library, doing research with Sam and Cas, he had read the same page of archangel lore about six times. It wasn’t like it was anything new, they had gone through this same lore about a dozen times already since living here, but there was always a chance they had missed something useful. Jack was in his room, attempting to use his powers to track Lucifer, with limited success. So far they knew he was in Europe, but Jack had never tried this before, and without a spell linking them like before, progress was slow going.

 

“I’m gonna get something to eat. Either of you want anything?” Sam asked, closing his book and filing it back away, both Dean and Castiel shaking their heads. “I might go on a grocery run later...I dunno guys. Until Lucifer makes a move, is this doing us any good? I’ve read through all these tons of times when we were trying to get rid of Michael.”

 

“Ditto, but what else are we gonna do? It’s not like there’s anything to hunt. Radar’s drier than ever. I had a guy call an hour ago literally  _ begging  _ me for a case, sounded like he was going to start crying.” Dean said, slamming his book shut and crossing his arms, frustrated. He hated feeling useless. “Crowley’s got bupkis on his end, and angels haven’t heard anything, no strange murders or other supernatural stuff to track the guy with...we’re stuck.”

 

The three men were all quiet for a moment, thinking. Usually, even if they were stuck with a big bad, there were other small things to do, cases to work, people to save. Castiel finally closed his book softly, standing up and putting it away before walking out of the room, trench coat flared impressively behind him. The brothers looked confusedly after him, then at each other. It only took a minute for him to return, his expression determined.

 

“On your way back, Sam, could you bring back pizza? And beer? And perhaps something sweet? Jack would like pepperoni. I am partial to pineapple and olives.” Castiel said, and both brothers raised eyebrows at him. “If we can’t do something useful, then I vote we do something enjoyable. What we’re in could be the calm before the storm, and I don’t see why we can’t have a movie night while things are quiet.”

 

“Yeah...yeah Cas, that sounds great.” Sam said, smiling and nodding. The room felt a little less stifling, like everyone had relaxed a little, and Sam found himself thankful for their friend. Sometimes he and Dean would get too stuck inside their own heads, and Cas helped to get them out. “Dean? Toppings?”

 

“Meat lovers.”

 

“Sounds about right.”

 

“Hey! Bitch!”

 

“Jerk. I’ll pick up pie too. Text me anything else you guys want.” Sam said, grinning at his brother’s red face before walking out. He knew Dean was still getting used to everything, and he hoped poking some light fun at him would help him relax. Cas was good for his brother, he didn’t need to read through a million books to know that.

 

Dean relaxed into his chair a bit while he thought about pie, then stiffened when Cas gently placed both hands on his shoulders as he stood behind him. The angel just smiled, gently rubbing and even starting to massage a little until the man relaxed under him, neither saying a word. Dean was going to have a rough time getting used to casual touching like this, both of them knew that without needing to speak, but they both wanted it. Castiel waited until he heard Sam leave the bunker before he spoke. 

 

“You do realize I could feel you longing for me all afternoon, don’t you?” Cas started, Dean shutting his eyes and trying to keep his heart from racing. He failed, and Castiel just smiled. “I can feel the differences in how you think of me. Today was very physical longing. You never have to be afraid to, it’s...very flattering, but also  _ distracting _ .” he continued, sliding his hands slowly down Dean’s chest, causing the other man’s breath to stick in his throat as he looked up into some very intense blue eyes. 

 

“I, uh...I didn’t mean to bothe-” he tried, but Castiel kissed him silent, gently moving their mouths together in a way that showed the angel was most definitely not bothered by it. Five minutes passed, then ten, but neither wanted it to ever end. Cas kept his hands moving and stroking across Dean’s chest and stomach, and gently pushed him down any time he tried to move or turn, burning his human’s arousal higher and higher as he was carefully handled the way Castiel wanted. Dean was leaking in his pants and straining to get some relief, but Cas just...didn’t let him, and somehow it made it ten times hotter, and by the time he finally spoke, he was panting. “Cas, holy shit, I need a break, please.”

 

“Was that alright? I’m not...I like the idea of controlling you, Dean, within reason, but I don’t know what your limits are, or what you’ll enjoy. I want to make you feel good, and you’ve given me the impression that you like when others...take charge.” Castiel said, very pleased with the flustered mess he had turned Dean into. He sat in the chair next to him, proudly showing how hard he was as well, and the hunter kept staring at the bulge with hunger.

 

“That,  _ all  _ of that, was insanely hot. Fuck, Cas, all you did was kiss me and grope me a little, you didn’t even touch my dick. I almost shot off just making out with you. That’s not...normal, for me, just so you know. But I don’t really know what my limits are, exactly. I’ve done a little tying up, been on the other end too, but fuzzy handcuffs are about as far into that kinda thing as I’ve gone. Always...always been interested, though.” Dean admitted, trying to get himself together.

 

“I may have done some internet searches last night...and while I’ve barely skimmed the surface, with this kind of thing, communication is very important. I want to know when I’m alright to do certain things, and when I’m not.” Castiel said, Dean just raising an eyebrow and smirking a little.

 

“What, like a safeword?”

 

“That is one option, yes. That is, if you want me to ignore most protests...and use you however I see fit.” Castiel offered, and Dean’s mouth dried up  _ real  _ quick. There was a fire behind Cas’s words, and he was starting to realize that just because Cas was less vocal or reactive than him, didn’t mean he wasn’t just as into all this as Dean was. It scared him, just a little, putting himself in someone’s hands like that, but given his limited experience with both Crowley and Castiel...he knew he enjoyed it. “Of course, as you said before, safe words don’t work when your mouth is full, and I would like it to be full often.”

 

“Jesus Christ, Cas, you can’t just  _ say  _ that.” Dean said, dick throbbing, looking around the library like Sam would be eavesdropping. His brother knowing he was dating Cas was one thing, knowing everything they did in the bedroom was another. “OK, yes, you’re right, we need some kind of system or something, alright? God, you’re driving me crazy. Can we talk about this...not in public?”

 

“You certainly didn’t mind it when I was kissing you just now, but alright.” Castiel said with a smile, getting up and holding out a hand for the hunter. Dean stared at it for just a second before taking it, and felt like a spotlight was being aimed directly at him. The bunker was quiet as they walked towards the bedrooms, it was just them around, but holding Cas’s hand made him feel like someone was going to jump out from behind every corner. But he held on, because he wasn’t a baby, and he liked the feel of the angel’s hand in his. Castiel surprised him by leading them into Dean’s room, letting go of his hand to shut the door behind them. 

 

“Alright, what kind of system did you have in mind, Dean?” Castiel asked, and the poor hunter just felt nervous. Lisa had been the only person he had been with long enough to work out any kind of ‘system’, and that was mostly so they could have sex when Ben was asleep or at school. This was...a different kind of system, and the amount of options and variables scared and excited him at the same time.

 

“Uh...geez, man, I don’t know.” Dean said, rubbing at the stubble on his cheek. Cas just stared at him in that unnerving way he did that made him feel tingly all over. Goddamn, he really had a thing for this guy, and hiding it was getting progressively harder now that he was actually  _ allowed  _ to show it. “Well, for starters, maybe no talking about sexual stuff around anyone else. You know, unless they’re like, one of the people we’re banging. Fair?”

 

“Of course, I know that kind of talk around others makes you a bit uncomfortable. What about things not sexual in nature?” Castiel asked, and Dean frowned in confusion. The angel stepped forward and gently cupped his face with one hand, stroking with his thumb, and Dean went red. “Like this. Or saying ‘you look very handsome today, Dean.’ If you would prefer me to refrain, I don’t mind, so long as I can do so when we’re alone.”

 

“No, no, I-” Dean started quickly, but had to clear his throat when his voice came out way too high. “That kind of stuff is fine, but just don’t overdo it. No showering me in roses, or any really girly crap. Kissing...maybe gimme a little time to wrap my head around doing that in public. How...how about you? Anything I shouldn’t do?”

 

“Sex is something most humans partake in, as is romance, and I have no shame for either. Unless there are children around, I’m happy to fornicate or show affection anywhere you would like, and have no issues with ‘PDA’.” Cas said, quoting with his fingers, and Dean had to shove images away of him pinning the angel up against a bookshelf or the kitchen counter and having his way with him. He was supposed to be the one who didn’t want those things, dammit.

 

“Good, ah, good to know.” Dean said, letting out a shaky breath when Castiel moved forward and gently pushed him against his bedroom door, holding him there lightly with his hand on his neck. A lotta blood started going south, and he had a hard time meeting Cas’s eyes as the angel slowly trailed his hand southwards as well.

 

“Dean, part of the reason I want something like a safe word, or a gesture, is that I can read how your body reacts to me. I’ve gotten quite good at it over the years, especially since I’m the one who remade this.” Castiel explained, his low voice almost a whisper as his hands traveled where they wanted, slipping under his shirt and making Dean hard. “When I first knew you, I thought you were afraid of me. Now I realize it was something else.”

 

“S’not my fault you were always pinning me against walls...” Dean protested lightly, feeling almost lightheaded. The angel just smiled lovingly at him, putting butterflies in his stomach. Just like in the library, Cas was teasing him, using light touches and caresses that were driving him insane. 

 

“My point is that your body may like the things I’m doing, but I still respect your choices. I am much,  _ much  _ stronger than you, Dean.” Castiel said, gently taking both of Dean’s wrists in his hands and pinning them above his head, the hunter’s eyes going a little wider. “I could keep you here, pinned against the door, and use you however I want. Without touching you, even.”

 

With that, Castiel stepped away, leaving a shocked Dean with his mouth agape when he found he couldn’t move his hands from the spot they’d been placed. It didn’t quite feel like something was holding them, more like there was some force pulling his wrists against the door. Dean looked up, but saw nothing, looking back down and going crimson when he saw Cas inspecting him, a smirk on his face. He was surprised how hot he found this, how hard he was being on display.

 

“I can tell you like this, by your heartbeat, your flush, even your smell. But I don’t want you to ever feel like you can’t say no, or decide you want to do something else. I’m extremely grateful, and lucky, to be able to do these things with you, and I don’t mind if you decide that you want to take charge and use my throat for hours on end.” Castiel said, laughing lightly at the groan Dean let out at the idea.

 

“Got it, my opinion matters, I got a voice at the table, when do we get back to the part where I can kiss you?” Dean asked, frustrated. Castiel just raised an eyebrow and ‘hmm’ed at him, walking closer but not letting him go. He gave a little groan when Cas started with his light touches again, getting louder when several gentle strokes to his covered cock were given. “ _ Cas _ !”

 

“This is a demonstration, Dean. You’re clearly enjoying this, but you also want to kiss me. I think we should have a signal, so I know when to let you go...or if I can just keep going.” Castiel said, firmly squeezing Dean’s straining cock and making the hunter cry out, working his hand across it over and over. It only took a minute to get him truly flushed and panting, when Cas watched with rapt attention.“Can I make you cum like this? I want to watch you.”

 

The request went right to Dean’s dick, and didn’t give him a choice, the hunter moaning loudly as he began to fill his pants with seed. Castiel’s hand never paused, and the two of them locked eyes as the angel worked him through his climax. Once he was done he was quickly released, and lunged forward to bury his tongue in Castiel’s mouth, feeling sticky and messy and fantastic. He pushed them both towards the bed, until he had pinned the angel on top of it.

 

“You are  _ so  _ gonna pay for that.” Dean threatened, not very intimidating when he couldn’t stop sloppily kissing the angel’s mouth, jaw, and neck. Castiel snapped his fingers then, and was completely bare, hard, and ready, and Dean froze at the image before him. It was like being at an all you can eat buffet and not knowing where to start. Castiel’s blue eyes burned into him.

 

“It’s a price I’m happy to pay. So, Dean...what would you like me to do?” the angel asked him, almost innocently, but nothing could look innocent with a body built for sin like that, a hard and leading cock standing at attention, looking like one of those models on those magazines Dean stayed away from. The hunter paused, still fully clothed, but forced himself off the bed so he could start stripping slowly, his skin celebrating the feeling of the cool air. His cock was slick with release, but still hard with Cas looking at him like that, cum all over his shaft and balls.

 

“How about you come clean up the mess you made, and I fuck another one into ya?” Dean ordered, throbbing slowly, unable to stop a small groan from escaping when Castiel got up and walked over to him, then slid to his knees. The angel admired his handiwork, then started sucking on the still sensitive head of the hunter’s cock, humming in amusement at Dean’s almost pained expression at the overstimulation. This humming was stopped when Dean put a hand on the back of Castiel’s head, shoving his friend down to the base of his cock and holding him there.

 

“This is supposed to be payback, no laughing.” Dean chastised, in awe of Cas’s ability to take his huge cock with such little trouble. He wasn’t bragging, dozens of women had choked and screamed and climaxed on his cock, and Cas was swallowing it like it was no big deal. The angel just stared up at him, his tongue moving back and forth as he attempted to do as he was told. “You know, this isn’t much of a punishment with you not having to choke on it.” he continued, amused, Castiel sliding off and looking thoughtful.

 

“I could choke on it, if I wanted. I could work to be a lot more ‘human’, like when I exercise. It’s not very difficult, when I get the hang of it.” Castiel offered, surprising Dean. The thought of Cas choking on his dick, or sweaty and panting...it gave him mixed feelings. He thought about how collected and in control the angel seemed, and it was kind of hot, but he liked the idea of being able to ravage the other guy too.

 

“I’d be alright to try it, Cas, but...I like you the way you are. I don’t want you to have to change, or do anything different, just because I might like it. If you think  _ you’d  _ like it, I’m all for it. Otherwise, I don’t think having a...partner, with no gag reflex, is something any guy can complain about.” Dean said, glad that when he gagged it just seemed to go right to his dick. 

 

Castiel didn’t respond for a while, making Dean let out little pleasured noises while he was serviced, the angel licking and slurping and sucking everywhere to clean up his mess. Dean had slept with a few women who really liked giving head, but none of them seemed quite as patient or exploratory as Cas was being, and Dean just slid his hands behind his own head and enjoyed the treatment. Other than Crowley, it had been so long since he’d had sex, and he’d missed it a hell of a lot.

 

“You’re incredible, Dean.” Castiel said, the hunter looking down at him with a little confusion as the angel gently stroked his heavy cock. “The feelings you make me feel, they’re so varied and unpredictable. Earlier, all I could think about was bending you over on a table in the library and sliding into you...but now, looking at you, I just want to keep doing this until you’re ready to spread my legs and just... _ use _ me. It’s very confusing, but in a wonderful way.”

 

Dean just bent down and hoisted Castiel up until he could slide his tongue into the other’s mouth, their hard cocks sliding between them as they ground themselves together. Arms grabbing, hips languidly thrusting, they just stood and enjoyed one another for several minutes. Dean just kept running both those scenarios over in his mind, and it was hard to decide which he liked better. It was still hard for him to admit it, but he really,  _ really  _ wanted to be fucked by Cas, but he knew he was great at fucking too, and he wanted to show his angel just how good he could give it to him.

 

Castiel broke off the kiss, frowning and opening his mouth, but the knock on Dean’s door beat him to the punch. Dean paled a little, but Cas just smiled, kissing him briefly again before bending down to retrieve and don his pants. He handed Dean his, the hunter scrambling to put them on when the other man went for the door, forgetting they were still a mess of cum inside. He was red all over when Castiel opened the door to reveal an equally red Jack, who looked nervous as hell.

 

“I’m sorry to bother you, I know you’re...doing things.” Jack said, looking a little ashamed, but it didn’t stop his eyes from eyeing both shirtless and clearly aroused men in front of him. Dean couldn’t make himself speak, both embarrassed and somewhat into the situation, despite trying not to be. “I think I know why I can’t get a lock on where Lucifer is. I think he has someone helping him, keeping me from seeing him. I’m not sure what to do now.”

 

“We’ll find him, Jack. For now, I think relaxation is a more productive way to spend the evening. Dean, how flexible are you with who we involve in our bedroom activities?” Castiel asked, putting an arm around Jack. The hunter’s eyebrows shot up, and Cas just smirked. “Who did you think the attractive young man I practiced with was? It’s been very hard on Jack, hearing us have fun without him. But if you’re alright with it, and would prefer it to just be the two of us tonight, I could just have fun with him myself, another time.”

 

“He...you...you’ve had sex?” Dean finally managed, the mental image making him throb in his slick jeans despite his surprise. Cas and Jack...that was a wet dream, which was appropriate, given the situation. Jack looked nervous and was blushing very hard, but smiled when Castiel rubbed his arm comfortingly.

 

“We didn’t go all the way, I wanted to save any actual penetration for my first time with you. But everything we could think of that wasn’t, strictly speaking, ‘sex’, we tried with much enthusiasm. Do you think you’d be comfortable attempting a threeway a little early? I don’t want to do anything that makes you uncomfortable.” Castiel said, and Dean felt his knees go a little weak. Jack was extremely handsome, and the idea of him and Cas having fun with him...taking turns on him...only reason he didn’t jump on it immediately was the fact that he’d cum once already, and that let a little rational thought into his head.

 

“Not that the thought of that isn’t one of the hottest things in the whole damn world, but...Jack, are you sure you’re ready for something like that? Sex is...well, it’s fun, but it’s kind of a big deal. And you’re still pretty young, I guess, for a Nephilim?” Dean said, actually unsure how their species counted age, exactly. Castiel was already working his pants open at Dean’s question.

 

“I already examined his mind, since I had those same concerns. But he’s mature enough to make these kinds of choices. He’s grown up a lot in such a short time, and since he’s experienced many of the negative aspects of adulthood, he might as well enjoy the perks as well.” Cas said, pulling out his hard seven inches and letting Jack start tentatively playing with it. The angel looked over at Dean, who was trying not to drool. “Do you feel like joining us, Dean?”

 

Castiel didn’t wait for an answer before pulling Jack into a deep kiss, shutting the door without breaking it off, and Dean realized this was sort of the moment of truth. If he said yes to this, if he accepted doing multiple guys at once so eagerly, he really was the slut that Crowley kept insisting he was. Granted, he’d had threesomes with women before, but this was different, right? Wasn’t it? 

 

“...fuck it.” Dean said, coming over to the other two men and only hesitating for a moment before starting to feel Jack up, the Nephilim moaning into Castiel’s mouth. Breaking off the kiss, Jack and Dean only paused for a few heavy seconds before delving into each other’s mouths, Castiel only interrupting so he could remove Jack’s shirt, which had Dean roaming around the younger man’s body with his hands and smirking. “Jesus, you’ve been packing on the muscle, kid. Guess I should thank Sammy, huh? I don’t know if I can handle the two of you.”

 

“We’ll go easy on you, Dean, if you want. But I don’t think you will.” Castiel said with a twinkle in his eye, before moving behind Dean, his hard cock pressed against the hunter’s jeans. The angel worked them open slowly with one hand, his other reaching forward to pull Jack closer to truly pin Dean between them, who was slack jawed at the fact he was sandwiched between two of the hottest frickin men ever. His teen self would have never dared to think about something like this. Castiel yanked down his pants the rest of the way, his fingers gently caressing his bare ass, then rested his steel rod against his cheeks and began grinding. 

 

“I know we’re waiting, but I’m very excited to get inside you, Dean. And to be on the receiving end, as well, but I think seeing your face when I push myself in...that will be very satisfying.” Castiel said, and Dean got chills all over. Cas slowly pushed Dean forward so he could get his dick into more sensitive areas, forcing the other man to hold onto Jack for support as his head was forced to crotch level. “Now, I think you’ve kept Jack waiting long enough, don’t you?”

 

Dean fumbled with the buttons on Jack’s jeans, his brain having trouble functioning with Castiel gently thrusting across his hole. The young man moaned quietly when his fly finally opened and let his big dick spring out into the air, making Dean open his mouth in both surprise and lust. The kid was bigger than Cas, almost as big as he was! Thick and rock hard, he looked like a cross between the hunter and the angel, the best of both.

 

“Dean, I...I had a hard time controlling myself with Nick, and I don’t want to hurt you.” Jack said uncertainly as Dean took a minute to pull both their pants down and off, the hunter managing to stay bent over and not fall with Castiel gripping his hips. “I don’t mind just watching, or just-” His words were lost when Dean just looked up at him with a smirk, then leaned forwards to take the head of his cock into his mouth, humming in pleasure around the thick appendage. 

 

“Dean is very good at sucking cock, even though he’s almost as new as we are. Relax and enjoy it for now, because I think he’s going to want you to fuck his throat after a while. He likes some rough treatment. Don’t you, Dean?” Castiel asked as he kept thrusting, and the meat of the sandwich just moaned an affirmative as he sunk down a few inches and just enjoyed the taste. Castiel didn’t sweat, or produce much precum, and Jack did both. “Jack is like me in some ways, Dean. I don’t know if you’ll have room for pizza after we’re done.” The thought of pizza had Dean pulling himself off Jack’s dick, much to the disappointment of the Nephilim, who looked like a kicked puppy. 

 

“Sam might be home soon, do we...I don’t want to stop, but he’s gonna come looking for us.” Dean said, separating himself from the other two, who’s cocks both looked red and angry. Dean had cum, they had not. Castiel looked frustrated, but turned to Jack, understanding that his thoughts on these things were different than Dean’s.

 

“Jack, you’ve been working on finding Lucifer’s location all night, can you do the same for Sam? See how far away he is?” Castiel asked, and Jack nodded, a little out of breath, before closing his eyes and concentrating. It only took a minute, but it was enough time for Dean to know just by the feel of his gaze that Cas wanted him bent over again, which made him shiver.

 

“He’s just leaving the grocery store...he’s going to pick up the pizzas. Last time it took him ten minutes to get home from there, so we should have about fifteen?” Jack said, mostly certain. Dean looked less certain, torn between not wanting his brother to be in the bunker while he was banging two angelic beings...and banging two angelic beings. Castiel gave a small sigh and walked over to him, putting his hand on his shoulder.

 

“Do you trust me, Dean?” Castiel asked, and Dean nodded slowly. Of course he did. The angel smiled, gently pushing down, and Dean dropped to his knees as he was guided, even as he felt his nerves buzzing. “Then you and I are going to help Jack cum, together, with your mouth and my hands. Then I’m going to take my turn and use your throat to cum as well, while you stroke yourself to completion, all before Sam gets home. Objections?”

 

Dean couldn’t make himself answer, but the smile on Castiel’s face was a sure one, and the angel motioned Jack over while his other hand went to the back of Dean’s head. Once Jack was close enough, the hunter let himself be guided forwards, opening his mouth and letting the shaft sink in. The Nephilim moaned, and although Dean gagged after the halfway mark, Castiel didn’t stop until he had that cock buried to the base inside him. 

 

“He’s so slick and soft, it feels amazing...” Jack groaned, Castiel letting Dean go, but he stayed there for another few seconds, enjoying the experience. His cock was hard as diamond, throbbing when he looked up to see the two of them start kissing. Dean started sucking then, a little slowly at first, then with enthusiasm, using his hands to help things along. He wanted Jack to cum, and that thought had his engines revved. “Castiel! Oh, don’t stop, either of you.”

 

Jack had a blissed out look on his face, and Cas was just smiling away, happy as Dean had ever seen him. Dean realized the reason he couldn’t see what Cas was doing, was that the angel was playing with Jack’s hole, forcing gentle gasps and startled moans from the boy and making him leak huge amounts of pre down Dean’s throat. When Jack started to pant and get a certain look in his eye, Dean knew the end was near. He couldn’t blame the kid, he was new to this, and being attacked from both sides. 

 

“I’m going to cum soon, keep going!” Jack ordered, squeezing his eyes shut and gritting his teeth, forcing his hands to his sides and trying not to make the same mistake twice. In no time he was blasting down Dean’s throat, the hunter swallowing the huge but manageable load, groaning in satisfaction as he gulped down everything he was given. Three huge mouthful later, he was helping Cas get a limp Jack on the bed. 

 

“There you go, Jack...does that feel better?” Castiel asked, brushing the boy’s sweaty hair off his forehead. The Nephilim nodded, out of breath and looking satisfied, despite his cock staying hard. Castiel smiled, but it disappeared when he looked at Dean, a glint in his eye that had Dean dripping onto the ground. “We have five minutes. Open your mouth.”

 

Jack had been trying to be careful not to be too rough with Dean. 

 

Castiel had no such reservations. 

 

Five minutes later, Dean had his own spit and sweat covering his torse, both hands gripping the angel’s massive thighs and failing to stop Cas from fucking into him like a rabbit on a mission. He gagged and choked often, Castiel knowing just when to stop so he could gulp down a little air before gulping down a lotta cock. He felt debased, used, and he’d never been harder in his goddamn life. Cas made very little noise, his face pure determination as he thrust, switching from both hands on the back of Dean’s head to one as it suited him, looking like he had all the time in the world to enjoy this slick fuckhole.

 

“It’s been five minutes...” Jack said absentmindedly as he jacked his cock to the sight of Castiel using Dean so roughly. He had assumed Cas was exaggerating when he said Dean liked it rough, but clearly, judging by Dean’s purple and dripping cock, that wasn’t the case...he resolved to use Dean the way he wanted to, next time. Castiel just looked up at the boy and grinned, making the hunter whimper around his dick.

 

“Until I hear the Impala’s engine in the garage, I’m enjoying myself. You should too. Why don’t you cum on his face, like I did to you? And Dean, he’s right, we don’t have long. Take your hand off my leg and make yourself cum on the floor, I’ll finish with you.” Castiel gently commanded, not even pausing in his thrusts as Jack came over, pumping his cock in front of his face. Dean barely got his hand around his own cock before the kid was blasting his face and hair with cum, forcing Dean to shut his eyes as more of Jack’s cum was pushed into his mouth by Cas’s cock.

 

“I can hear Sam pulling up, Dean, get yourself off or we’re going to leave you like that during dinner. I’m cumming  _ now _ .” Castiel said, unable to keep silent as his orgasm approached, low grunts making Dean start to furiously stroke his neglected cock. Cas cursed through his teeth as he started unleashing his cum into the human hole beneath him, then laughed victoriously as Dean shook and bucked with an orgasm of his own, but didn’t stop pumping his hunter full until the other man was desperate for air. He painted Dean’s face and chest with the rest of his seed, making the most beautiful mess.

 

“Jack, clean yourself up and go help Sam with the groceries, please. Say we’ll be there in a few moments, with no mention of what just happened.” Castiel said, not even out of breath, helping Dean slowly to his feet as Jack did as he was told. Dean was shaking, and dripping with cum and other fluids from head to toe, but Castiel cleaned him up with a gentle touch of his fingers to Dean’s brow. 

 

“...oh thank fuck, I forgot you could do that for a minute.” Dean said roughly, relieved but exhausted. He looked at their clothes strewn across the room, shivering again, but the angel just gently stroked his face until their eyes met again. “I wasn’t kidding, Cas. I don’t know if I can handle this. That was insane, and aggressive, and...I don’t know how to deal with how much I liked it. You made me your...”

 

“My bitch? I did. And yes, you enjoyed it. But there’s nothing wrong with what we just did. You enjoyed it, I enjoyed it, and so did Jack. Which is the point, I believe.” Castiel said, pulling the human into his arms, letting him gently shake against him. He stroked Dean’s back and held him until his breathing evened out. “It’s alright to be nervous, this is new to me too. Was I too rough with you?”

 

“No, god no, it felt like my dick was gonna go off every time you...I don’t know if I’m gonna be able to go out there like this, Cas. I’m clean, but my voice...and my legs won’t stop shaking.” Dean said, his throat clearly well fucked, which made Castiel just a little happy. He placed a couple fingers on Dean’s neck, and the hunter cleared his throat a couple times, then looked down at his suddenly less weary legs as he spoke normally. “...thanks, Cas.”

 

“I don’t think you give your brother enough credit, but as long as you want to be discrete about things, I will help however I can. And...again, Dean, please tell me if I do something you dislike. You being happy is the most important thing to me.” Castiel insisted, and Dean practically melted into his arms, kissing him deeply for a moment before looking at his clothes on the floor.

 

“Alright...let’s go see if I’ve still got room for a slice or two of pizza.”

 

(Dean ate four)

 


	18. Character Stats!

**Summary for the Chapter:**

> Stats of all the hunky guys in my fic. You already know the basics of what they look/act like, but here's all of it in one place for anyone who needs/wants it. NSFW!...but if you've read my fic, you already know that.

Hey there everybody, this is just something I thought you guys might like or find helpful. You know all these characters pretty well, but this will include anything I think you need to know, namely anything sexual in nature that we don't get in the show, or things in my specific world.

**Dean Winchester:**

Sexuality: Bisexual

Role: Vers Bottom

Physical: 6 feet and 1 inch of hot, male model goodness. Always kept in great shape by hunting, with a bit of a softer belly from all the diner food. Lately, Dean's been increasing his muscle with weight lifting, and his arms and chest are getting even more impressive.  He's got a dick size of eight and a half inches, nine at max hardness (we're talking red, leaking, painful erection people). Thick and meaty, and fond of leaking like a faucet, Dean already had a hard time hiding his reactions to pretty women. Now that men are in the picture, and they want him? Yeah, one look at the tent in his pants is all it takes to tell he's interested. He's also got thick thighs, and an ass that was made to be used and abused. Despite his lack of experience, he's also one of the best men around at giving blowjobs, his enjoyment and enthusiasm obvious. While he's incredible at topping men and women, having left dozens of one night stands who still drip at the thought of those nights, Dean just loves to be dominated and fucked. He doesn’t love to admit it, but he can’t help but enjoy it, so much so that he can sometimes orgasm just from getting one of his holes stuffed.

 

Castiel:

 

Sexuality: Pansexual. 

Role: Vers top.

Physical: Just an inch shy of six feet, Cas might be a little shorter than the Winchesters, but you wouldn’t know it by standing next to him. And once those clothes come off...hoo boy. In his clothes, he looks like a handsome accountant. Without them? He’s all tan muscle, built more like a god than an angel. His cock is seven inches of absolute steel, with a slight upward curve that he uses to great effect, able to read his partner’s (especially Dean’s) reactions to what he does, and hit your sweet spot every time. While perfectly willing to be submissive, he prefers to be the dominant one in the mix, especially when it comes to Dean, who’s submissive aspects compliment his dominant ones beautifully. He’s very in shape and toned, but it’s his nature as an angel that grants him his supernatural stamina. Able to control his orgasms and many of his other physical attributes, Cas can literally go all night long...or at least until Dean’s had that fifth orgasm fucked out of him. While he enjoys sex in general, his main enjoyment will always be Dean.

 

Jack Kline: 

 

Sexuality: Demisexual.

Role: Versatile. 

Physical: Jack aged himself somewhere in his early twenties, and gave himself a sexy bod to boot! Once he began training as a hunter, he built up some muscle, but is still slighter than most others around him. However, as one of the strongest beings on the planet, it’s best not to underestimate this 5 foot 10 inch powerhouse, especially when you see what he’s packing below the belt. Eight inches of thick, hard fury that Jack just loves to use. Willing to try almost anything that sounds fun, and slowly learning to learn to use his powers, it’s hard to think of something Jack isn’t capable of in the bedroom. As with his powers, Jack’s inexperienced nature sometimes means he needs a little direction, but he makes up for it with eagerness, especially when he can fuck a tight hole. He likes being serviced, especially by Dean, who finds the Nephilim’s sometimes selfish attitude to be hot. But when it comes to Castiel, Crowley, and sometimes Dean, he defers to their judgement and takes their lead, happy to be on the receiving end from men who are so eager to make him feel good.

 

Crowley: 

 

Sexuality: Bisexual.

Role: Vers top.

Physical: While quite handsome, most would find Crowley’s 5 foot 9 inch figure rather unassuming. This is a dangerous mistake, as any person charmed into Crowley’s bed will soon find themselves in for the ride of their lives. An entire foot long and massively thick, Crowley’s monster cock is only half the reason he’s one of the world’s best sexual artists. Crowley has made it a habit to figure out exactly what a person wants, which is useful for both professional and personal reasons. This is one of the reasons he’s so interested in Dean, because the man’s desires and what he actually  _ does  _ have conflicted so heavily in the past. Mostly dominant with his partners, this goes a step further with the hunter and his angel, as their past as enemies makes sex even more exciting. Slightly round around the middle, Crowley’s tattoos, suit, and powerful arms give him the look of a powerful businessman who needs to relieve some stress...which Dean is very into. It helps that he’s objectively one of the best kissers in the known universe, and one of the most well versed in the bedroom, second only to Gabriel.

  
  


Chuck (God): 

 

Sexuality: Bisexual.

Role: Top.

Physical: I mean...he’s God. Technically able to look however he wants, the form that he has now, as Chuck, is the ultimate Daddy. 5 foot and 8 inches of muscled goodness that he likes to show off with tight shirts, Chuck likes to be worshipped. A little understandable, all things considered, but he gets upset when others don’t see it that way. He has a thing for being in control, almost to a fault, but most people find it hard to complain when they’re being stretched out on a cock thicker than a beer can. A little over six inches long, most are lucky to get two inches of him without some supernatural assistance. A fickle lover, sometimes he wants to get off in five minutes and be done, other times he wants to lay into you for six hours until you’re a gaping, overflowing mess of his cum. He can do almost anything with his power, but it all depends on the mood he’s in. He has a bit of a preference for how a pussy feels, so occasionally he’ll change his male partner’s genitals, remembering to change them back almost every time.

 

Lucifer: 

 

Sexuality: Bisexual? Worshipsexual? Hatesexual?.....“complicated”.

Role: Versatile.

Physical: 6 foot 1 inch of powerful, archangel dilfness, Lucifer is like your friend’s dad with the big arms and beer belly that you know you shouldn’t be attracted to. And who fucks the living shit out of you in the garage when you’re both a little too tipsy. Often morose or annoyed at something, sex is a great way for him to let loose, and is one of the few things about humanity that he enjoys. While inexperienced, his enthusiasm and vigor make up for it, and he loves pummeling a hole doggystyle for hours to get out his frustrations. And with his thick, eight inch sausage, his partners have a hard time staying quiet, which he takes a lot of satisfaction in. Much to his chagrin, however, Lucifer also loves bottoming, unable to resist when someone wants to give it to him for a change. He often tries to keep control of the reigns in the bedroom, but it’s hard to do when you can’t stop cumming on your partner’s dick. Lucifer has an unhealthy obsession with getting Sam to sleep with him, their past in hell making things more complicated than the Winchester would like.

 

Gabriel: 

 

Sexuality: Pansexual.

Role: Vers top.

Physical: 5 feet and 8 inches, with a hard seven incher, Gabe is one of the smallest in the group. And everyone has learned, very quickly, that underestimating the archangel when it comes to anything sexual is a mistake. His body is close to perfect, not skinny or bulky, not smooth or hairy, but juuuuust right. Gabriel was the first amongst angels to try sex, and he’s kept up a hedonistic lifestyle since humanity invented the hookup. The most experience out of any being, his own father included, Gabriel is able to use his powers for almost anything a person could fantasize about. And several dozen things no one’s even thought of before. Duplicates. Sex changes. Growth and shrinking. Not to mention his raw skill in the bedroom without any powers, his tongue and lips having inspired more poems and love letters throughout time than he can keep track of. His father and Crowley both have a plethora of knowledge and skill when it comes to sex, but both must make way when it comes to Gabriel. That being said, sometimes he doesn’t feel the need to put in a huge amount of effort, content to just enjoy a regular romp in the sack. Usually on top, Gabe doesn’t dominate in the same way others typically do. He’s more laid back, less rough, more like the Hermes to his father’s Zeus and brother’s Ares, prefering to have his partner’s come undone because of his skill and precision. 

 

Sam: 

 

Sexuality: Heteroflexible. 

Role: Vers top.

Physical: 6 feet 4 inches of raw, muscled power, Sam is the most physically intimidating of anyone in the group. Hunting, healthy eating, and regular exercise have given Sam the perfect body for sex...but he got the ten inch, beer can cock from his dad. While mostly into women, he’s let the occasional man drop into the mix, and enjoyed himself well enough. Normally the more sensible and reserved brother, his and Dean’s roles somewhat switch in the bedroom, with Sam letting loose and dominating his partners with everything he has. So far, he’s never gotten a complaint, but it’s hard to work up a protest when you’ve lost count of the number of orgasms you’ve had on the Winchester’s massive dick. Extremely passionate, he always makes sure his partners are taken care of and satisfied, and doesn’t hook up lightly. He’s aware that Lucifer has a thing for him, and not happy about it, despite the fact that years of time in hell together has given him a sort of Stockholm Syndrome when it comes to the hunky archangel. 

 

HERE’S WHERE I NEED YOUR HELP AND INPUT

 

Sam is a very sexual person, we know this from canon, but he doesn’t delve into that as much as his brother. Because of what’s going to be happening in my fic, Sam’s going to have more of an opportunity for things like that, but I’m debating what would work best. I could have a way for Eileen to come back and for that to be a thing, and just leave Sam’s sexual life off to the side. Or, I could involve him with all/some of the guys who will be in my fic. This could or could not include Dean. I personally have always been on the fence about Wincest, as I see them as brothers who have a much more complicated and intimate relationship than most normal siblings (I mean, seriously, they were like each other’s only constants throughout their entire lives, up until maybe Castiel). So I would like your opinion on the matter, on whether or not to include Sam in the mix of guys, and if so, if that should include Dean. Also debating if John should ever be involved, because death is meaningless in SPN. Let me know in the comments please!

 

**Notes for the Chapter:**

> I'm almost done with a chapter that has actually story in it, but I figured I would do this in the meantime.


	19. BBQ Brothers

**Summary for the Chapter:**

> Jack gets an interesting request. Meanwhile, his dad and uncle have a heart to heart. (there is M/F in this chapter! You've been waaaarrned!)

**Notes for the Chapter:**

> Like I said, explicit M/F with an OC female character. Sorry this took so long, anyone else notice the world's going crazy? Keep your heads up, we're gonna be OK.

Jack appeared at Bobby’s front door, smiling to himself at how much easier flying had gotten now that he was used to it. Looking around the salvage yard in the sunshine, he could see why Sam and Dean had enjoyed this place growing up. Even with all the scrapped cars, there was something homey about it. He knocked on the door, unsure of why he was here, but always happy to see Bobby or Mary...but neither of them were the ones who answered the door.

 

“...Charlie? What are you doing here?” Jack asked, not unkindly, stepping inside when the redhead made room for him. She looked better than the few times he had seen her, but maybe a little nervous. Mary walked over from the kitchen before she could answer, giving Jack a big hug, and Bobby lifted a cup of coffee in greeting from behind her. “Is everything alright?”

 

“Yes, Jack, everything’s fine, but we did have something we were hoping you could help with. I know we ask that a lot, and if you’re too busy with Lucifer, then we understand.” Mary said, stepping back and looking guilty. They had spent a little less time together lately, with everything going on with the newly returned archangel, and she worried Jack might be feeling used. The Nephilim just smiled and shook his head.

 

“I don’t mind. We’ve hit a bit of a...snag, with my father, and I like being useful. What did you need?” Jack asked, and they all started walking into the kitchen, sitting down at the table while Bobby leaned on the counter. Mary’s touch could be felt in the place now, some newer appliances and pictures dotting the areas, but it felt much the same as the first time Jack had been here.

 

“Ya know how you helped me and my other self out? Did the ol’ switcheroo, so he could be with his wife and son and I could get outta angel prison?” Bobby asked, and Jack nodded with a smile. It had been difficult, but worthwhile, seeing everyone so happy afterwards. It had been a good way to develop his powers as well, everything seems a little easier since Crowley had helped direct him. Bobby looked over at Charlie before sipping his coffee, and Jack turned his attention to her.

 

“Well...I was wondering if you might be able to do the same thing...for me? I had someone special in our world...Kara. And a few days ago, Bobby told me about what you did for him and, well, the other him. And I couldn’t get it out of my head for some reason, until it clicked. If I die in this world-which, let’s face it, is pretty likely-I won’t ever see Kara again. She’ll be in one heaven, and I’ll be in another. Always apart, forever.” Charlie said, staring at the table and clearly picturing whoever this past love was. 

 

“So, you want me to go and take Kara’s soul from the other world, bring it to this one, then switch your place with the Charlie of this world?” Jack asked, and Charlie took a deep breath before nodding her head, looking scared and hopeful at once. Jack thought about it for a moment, thinking about how far he had come, and wondering if he would need help like last time...after a short moment of focusing, a golden rift opened to his right, surprising all in Bobby’s kitchen, and he smiled. 

 

He could do this.

 

______________________________________________________________________________

  
  


Castiel was trying, really trying, but he couldn’t stop smiling whenever he looked at Dean. For the hunter’s sake, he was doing his best to keep it to a minimum when they were around Sam, but it was difficult. True, Dean wasn’t yet comfortable with having sex when his brother was in the bunker, despite Castiel insisting either he or Jack would be able to stop any loud sounds any party might make, but Dean had given nervous acceptance to sitting together for movie night, and mostly clothed cuddling with him after. It was slower going than Castiel would have liked, but it was progress.

 

Jack had thankfully understood that the two of them needed time to themselves, but that there would be many times in the future where one, the other, or both of them would be happy to ‘get with’ him, as Dean had put it. Castiel was excited to do things with Jack, Dean, and even Crowley, surprisingly. But he was sure to make it clear to Dean that he and his comfort were his priority, and if anything needed to stop or change, it would.

 

The internet was providing no answers as to Lucifer’s whereabouts, but all three men kept at it while Jack was away, knowing that even if they managed to find Lucifer, the Nephilim would be likely be the one dealing with him. They could suffer through boredom and do their part, although Castiel had requested they at least liven it up with some music. To the Dean’s horror, ‘liven it up’ meant playing mostly instrumental or classical music, but both Winchesters were surprised to find that it helped them focus and relax...which may or may not have been the angel’s intent all along. 

 

“I’m just saying, some Led Zeppelin would be a little more-” Dean was saying, interrupted by Jack walking in with a smile on his face, looking around at all three of them rather expectantly. Dean attempted not to think about what the Nephilim looked like naked, and cleared his throat. “Uh, hey, Jack, you’re back early. Everything good in South Dakota?” 

 

“Very, Mary and Bobby are both doing well, and I did something that I think you all will like. At least, I hope you will, since you did last time.” Jack said, frowning briefly before his smile returned, confident that they would. He had managed to do it all by himself, without the surprise Bobby had gotten when he’d been zapped back into a body with no warning. The three of them waited a moment, before Sam finally spoke up, looking concerned.

 

“You, uh...wanna elaborate on that, Jack? Did you buy us some snacks, or something...bigger, like Bobby’s house?” Sam asked, hoping it wasn’t anything too crazy, despite trusting that Jack had the best of intentions. The grin he got from Jack was slightly worrisome, but then Charlie walked in, wearing a ‘I let the Wookie win and all I got was this lousy T-shirt’ shirt, and all three men relaxed a little, getting up to greet the redhead. “Charlie, what brings you-”

 

Sam knew something was different the minute Charlie hugged a confused looking Dean, considering this Charlie had never been much the hugging type. His mind reeled while he took in her outfit, the way she held herself, and the slightly teary smile she had on her face. The younger Winchester rolled what Jack had said over in his mind, and felt a surprising lurch of hope and excitement growing in his mind.

 

“Charlie?” Sam asked, the hacker extraordinaire turning to him, giving him a smile so sincere he felt tears coming to his eyes. He knew, he could see it in her eyes. 

 

“Hey, Sam...been a while.” Charlie said, and seconds later Sam nearly bowled her over with his hug before actually picking her up and squeezing, both Dean and Castiel looking at each other and trying to figure out what the hell was going on. Charlie looked at them both over Sam’s shoulder, finally crying, and let out a slightly sob filled laugh. “I’m back bitches, miss me?”

 

“Charlie? Like,  _ Charlie,  _ Charlie?” Dean asked, finally catching up, waiting for her to nod happily as Sam put her down, and then Charlie was almost tackled for the second time by the other Winchester, who hugged her properly this time. Castiel walked over to Jack and put a hand on his shoulder, smiling at the exchange. Dean looked at the two angelic outliers, and motioned them over as he squeezed Charlie. “Get over here you two, this is gonna be the only group hug I’m giving out this century.”

 

Everyone laughed as the poor super geek was dwarfed by tall, hulking men, and Charlie quickly recommended celebratory beer they had brought with them. Dean yelled his agreement, making Charlie shriek as he picked her up and slung her over his shoulder, everyone else laughing and following them, and soon everyone was drinking and snacking in the kitchen. 

 

“...never really seen anyone else outside the LARP camp, let alone had someone knock at our  _ door _ , and then this guy shows up with someone who looks exactly like me! Let me tell you, I have seen enough other ‘me’s’ to last me several lifetimes.” Charlie said, sitting up on the counter while everyone listened to her recount Jack’s offer. “She did seem pretty badass though. And apparently has as much game as I do, because the girl she was with...whoo boy. If my mom hadn’t been there...”

 

“Waitwaitwait, so you’ve got some kind of ‘Super Medieval Heaven Roleplay’ camp or whatever for nerds up there? Not that it doesn’t sound awesome, but I thought only soulmates could share heavens.” Dean said, looking at Sam who nodded in agreement. Their heavenly experience had been mixed, but they figured they had a better understanding than most.

 

“That’s what we got told it used to be like, but some guy named Ash has been connecting ‘like minded’ people’s heavens together. I’ve been hoping to meet him sometime, but he’s a busy guy. Used to be hard to do it, but with so few angels, they kinda have to leave him and all the people helping him alone, so it’s happening all over.” Charlie said, popping a chip in her mouth while Sam and Dean grinned at each other.

 

“Yeah, we know the guy. We knew him when he was still kicking it down here, mullet and all.” Dean said fondly, missing the guy a little. He was weird, but reminded him a little of Charlie, now that he thought about it. The idea of them teaming up was mildly terrifying. “Glad to hear he’s making things better up there.”

 

“And you were just...alright with leaving? I don’t want to be a downer or anything, but I’d have a hard time leaving our mom if the situations were switched.” Sam said, Dean nodding in agreement. Their mom and dad had a shared heaven, so it probably would have been even harder for them, whereas Charlie’s parents didn’t.

 

“Jack said he could take me back to visit, since he apparently figured out how to take a soul out of someone’s body? So I’m still gonna be able to see her, and my dad too! I didn’t get to see him while I was up there, except in some of my memories, but I shut that down pretty quick. No fakes for this girl, thank you very much. And besides...I missed you guys. I haven’t had enough adventures and quests and Comic Con panels yet. So you bitches are stuck with me for a while.”

 

“Damn straight. But how did you even find her? Aren’t there, like, billions of those rooms up there?” Dean asked Jack, who was sitting almost too close to Castiel, but not quite inappropriately so. He wondered if they were doing it on purpose, trying to make his mind wander, and Castiel’s occasional smiles to Dean had him thinking it was.

 

“I asked an angel to direct us. They were very helpful, but they kept asking me to ‘take the throne’ and other stuff. I told them I wasn’t really interested, but I’d ask Castiel if I could do anything to help when I got back. Heaven was...nice, but it seems a little boring, except for people’s personal heavens. I want to visit my mom the next time I go, if that’s alright?” Jack asked, Castiel smiling somewhat worriedly.

 

“Of course, Jack, and we can see what we can do about helping the angels. There aren’t many of us left. I just wish you had asked before going up there without me, the other angels are somewhat desperate, and that can make them dangerous.” Castiel replied, proud of Jack despite his worries. He was coming a long way, and his desire to help people was strong. 

 

“I understand. Next time, we’ll go together. I’m sure my mom would love to see you too.” Jack said, trying not to frown when he remembered what had happened the last time they had visited, when the Empty had come for him. He wanted Castiel to be happy, but he didn’t know if that meant he would be taken away, since Castiel seemed happy now. Similar thoughts were in Castiel’s mind, but he just smiled and patted Jack on the shoulder again.

 

They would deal with that when it came to it.

 

______________________________________________________________________________

  
  


The country music was too damn loud. And too damn country.

 

Lucifer stewed in his seat, arms crossed, looking rather like a petulant child while people drank, ate, and generally had a good time around him. The bar was, frankly, a shithole, and Lucifer had been to some doozies, namely hell. He would give anything to leave, or maybe burn the place to the ground. But the delightful reason he was here was busy bringing over ribs and beer, his face way too cheerful under that cowboy hat.

 

“Come on, Luci, you’ve got to lighten up. You haven’t cracked a smile at any of the joints I’ve taken you to, and every one of them’s got the Gabe Stamp of Approval. That doesn’t come easy. Now come on, this place has got the best barbeque this side of the Mississippi.” Gabriel said, plopping down his heaping basket of meat and tasting the sauce that had managed to get onto his finger. Lucifer eyed the food and drink with slight revulsion. He had needed to eat when his grace had been depleted, and it hadn’t been pleasant...but it  _ had  _ been dumpster food.

 

“Look, Gabe, I appreciate your whole ‘brother bonding’ shtick, but do I look like Dean Winchester? Don’t answer that.” Lucifer warned when it looked like his brother would happily comment, knowing his attempt to look threatening fell flat. For once, he was the weak and vulnerable brother, and they both knew it. “Point is, I don’t do the whole ‘eat, drink, and be merry’ deal. Especially the merry, unless there’s some maiming involved.”

 

Gabriel drank a few gulps of his beer as he thought, munching on a fry and giving his brother a stare that made the other archangel bristle. They hadn’t talked much, this last week or so, the days running together as Gabriel took them to different places with different time zones. He was letting his brother think, but it didn’t seem to be getting him anywhere. Lucifer was stuck, finally out of excuses. Their last conversation before his death bounced around in Gabriel’s mind as he munched, all the things he had let loose on Lucifer, but for the first time...he had just a little bit of hope.

 

“Look, Luce. We’ve both kind of been given a second chance here-”

 

“Which you still won’t tell me anything about, you death dodging, sugar coated-”

 

“My  _ point _ , brother, is that it hasn’t worked. None of it. None of your plans, none of your ideas for what you thought you wanted. Right? Please, stop me if I’m wrong.” Gabriel said, giving a hands off gesture and waiting for Lucifer to comment, which he did not, choosing to sulk and eye his silverware instead. “You’ve got nothing. No plan, no trick up your sleeve, no friends except for yours truly. And a son out there who’s got one hell of a bad image of you in his head, pretty justly deserved.”

 

“I’m sorry, was this supposed to be cheering me up? Because unless this ends with this place as a pile of ashes-”

 

“Would you  _ shut up _ , and listen to me, for once?” Gabriel said sternly, most of the bar patrons looking up as the lights flickered, Lucifer finally deigning to give his brother a reluctant stare. The Trickster shook his head and folded his arms like his brother, both just looking at each other and feeling the weight of their age as the world kept spinning around them. “I want to help, Lucifer.”

 

“Come on. After all that hate thrown at me in Apocalypse World? You’d help me off a cliff, maybe.” Lucifer said without much conviction or sass, the wounds still fresher than he would have liked. Gabe had really let him have it over there, nothing held back. And the worst part? As much as he wanted to deny it? Gabriel had been right. Maybe he was a cancer. Jack certainly seemed to think so. 

 

“And you know what? You’d deserve it. But this isn’t about what you deserve. Frankly, after all the crap I’ve pulled, I wouldn’t sittin’ pretty if I got what was coming to me either. This is about doing something neither of us have been any good at before.” Gabe said, sliding the ribs towards his brother, who eyed them before meeting Gabriel’s earnest eyes. “Change.”

 

Lucifer looked at the offered meal for a solid minute before realizing he had nothing left to lose, and with that depressing thought, he picked up a sauce covered rib with two very hesitant fingers. He sniffed at it, before gingerly taking a small bite off the bone and working it around in his mouth, trying not to notice Gabriel smiling as he sipped his beer.

 

“So, what kind of grand change are you proposing? Outlet mall for some new duds? Haircut? I’m thinking highlights, maybe some frosted tips.” Lucifer said with false excitement, annoyed that he found the flavor agreeable, and tried to take another bite as unenthusiastically as possible. It helped if he pictured it was the flesh of his enemies. Gabriel finished his drink and smirked.

 

“More like a change of mindset, but we definitely need to work on your whole ‘frumpy dad’ vibe you’ve got going on too. Picture this for a minute: You’ve beaten the Winchesters.” Gabriel said with a sweeping hand knocking over the salt shaker, Lucifer smiling in spite of himself as he took another, bigger bite of rib, relaxing a little as he leaned back.

 

“Liking where this is going.”

 

“In fact, you’ve beaten everybody. No more angels, no more demons, no more humans...even dad’s run for the hills, never coming back. Just the world as your oyster.” Gabe continued, knocking over the pepper, ketchup, and mustard, and making the hot sauce bottle hop away as he listed each of Lucifer’s past targets. Lucifer started picturing himself on a throne made out of the corpses of those he hated most. Maybe each of the Winchesters as the armrests, Crowley under his feet...he’d have to find a place for Rowena.

 

“Alright, love it, love it. I’m guessing there’s a ‘but’ in there somewhere I’m not gonna like.”

 

“No, no buts. That’s the story. What happens next?”

 

“Then...” Lucifer started, his smile fading just a little bit as he started getting a sense of where his brother was going. “Then I rule.”

 

“And what will that be like? Was always curious what your ‘perfect world’ would be, what the plan was after you beat Michael.” Gabriel said, only sounding a bit sarcastic as he snatched another fry and resurrected the vanquished ketchup bottle. Lucifer was silent for a moment, but his brother didn’t pry, just squeezing out some ketchup and enjoying the atmosphere while he waited.

 

“Like you said, humans and demons, poof, gone. But angels...I mean, there’s so few of them left, I guess they could stick around. You know, cause I’d still need someone to actually ‘rule’, right? If you play your cards right, I’d probably let you have Madagaskar, or maybe Australia; somewhere with a lotta those weird animals you like. And Jack would be with me, of course, if I can get him on board with the whole ‘master plan’. And no, I don’t know how. The Winchesters have got him wrapped around their trigger happy fingers.” Lucifer said, realizing that his plan was already a little different than when he had first gotten out of the cage nearly a decade ago. It had changed without him even realizing it. Gabriel was nodding thoughtfully.

 

“No bad, not bad. So, what would your typical day look like, in this perfect world?” Gabriel asked, innocently, Lucifer bristling inwardly. He knew what his brother was doing, trying to get inside his head. What worried him is that, long ago, it had sometimes worked. Michael, Raphael, even their dad...Gabriel could occasionally be very convincing, even to them.

 

“Oh, you know, start with a brisk morning jog through the Milky Way, maybe take a quick dip in a black hole. Show Jack how everything works, teach him things humans are too stupid and primative to have any idea about. Organize all those natural disasters, but without humans and their junk screwing everything up, it’ll probably be pretty easy. Get some praise from my little group of angels...sounds pretty sweet to me.” Lucifer said, smiling as he pictured Jack looking at him like he looked at the Winchesters and their pet angel.

 

“Huh...pretty picturesque. No pollution, no war, no corruption...” Gabriel said, nodding as he chewed on a fry. Lucifer felt just a little smug inside. “...no video games, or books, TV, or any of the other stuff Jack probably likes. Just you teaching him about how things work...like a school you can never leave. And I gotta say, Luce, I wouldn’t expect you to give up any of your favorite hobbies. Eternity without torture and murder? I didn’t think you had it in you.” Gabriel continued, knocking the smile off Lucifer’s face as he thought about eternity with no one but Jack and a few angels that his son would probably not want hurt. 

 

“That’s...I wouldn’t-”

 

“Your plan? Blows, brother. Blows big time. And not even in the fun way.” Gabriel said, Lucifer glaring at him for a minute before sinking back into his pouting posture, arms crossed and leaned back. Gabriel shook his head, smiling. “Lucifer, I’m not trying to be the little angel on your shoulder, pun intended. Do you think my nose is clean in all this? That I’m some little goody two shoes?”

 

“You certainly seem to have that ‘heart of gold’ thing going for you. The Winchesters trust you, not that they’re the brightest berries on the bush.” Lucifer mumbled, remembering how long he got away with possessing Castiel before Dumb and Dumber found out. 

 

“Bro, yeah, I try to be decent when it comes to the big stuff, but you’ve kinda been cooped up while I’ve been out here living it up. You don’t know the things I’ve done, the fun I’ve had...or the people I’ve punished.” Gabriel said with an eyebrow wiggle, Lucifer just rolling his eyes in reply. “Seriously! I was there, in case you forgot. I was with you in Heaven, then Earth before humanity, saw it all, got the T-shirt. And let me tell you, before humans, no more how many frills dad put on either one of them, they were both the same:  _ Boooooring _ .” 

 

“But what is so  _ interesting  _ about them?” Lucifer asked desperately as he leant forward, a fire in his eyes. Loud enough that a few people looked over, but a wave of Gabriel’s hand had them losing interest. “What makes you and dad so fucking gungho for these fleabags? They’re disgusting, violent,  _ weak  _ bags of bones! All they do is murder and fuck one another! What the hell did he see in them that he couldn’t get from...us?” he continued, growing quiet at the end. They both knew he’d meant ‘from me’.

 

“Because dad was right, Lucifer. Not about everything, and he did a shit job handling all sorts of stuff, but about humans he was  _ right _ .” Gabriel insisted, Lucifer just leaning back and not looking at him. There were tears in the elder’s eyes, and his brother sighed. “I know that’s not what you want to hear, I know I’ve told you this before, but it’s true. Yeah, they’re selfish pricks, but so are we. And there’s something you can learn from these fleabags, brother. You can try to be better. If not for yourself or anyone else, then for Jack.”

 

Lucifer was quiet for a long time, before finally looking at his brother.

 

“What do I do?” he asked quietly, and Gabriel grinned, looking over at an attractive blonde at the bar, next to her musclebound, douchey looking date with a too tight tshirt.

 

“Let’s start with some of the more fun parts of humanity.”

 

\---------------------------------------------------------------------------------------------------------------------

 

Her name was Cindy, and she had already cum twice on Gabriel’s tongue before ten minutes had passed, her fingers gripping his head as she cried out loudly in the bathroom stall. Her legs were propped up by some railing and Gabriel’s shoulders, and Lucifer just watched intently from the open, saloon style door of the stall, his dick stiff in his pants. The Trickster’s tongue was like an artist’s paintbrush, and Lucifer wondered if he could ask his brother for some pointers.

 

“Oh please, honey, you’re better at that than my beau, but I need a break!” Cindy begged, Gabriel pulling himself off her with a last lick and grinning. It had been too long since he’d done something like this. He gave her a considering look, eying every inch of her.

 

“Well, how about some cock?” Gabriel asked, Lucifer’s eyebrows going up, surprised when the woman let a smile grow on her face and nodded. She squealed as Gabriel lifted her up and put her legs around him, working on getting his belt undone as he moved her out of the stall and past a bemused Lucifer, setting her down on the counter and locking lips with her. He had dressed for the occasion, with jeans and cowboy boots, and Lucifer got a nice eyeful of smooth ass when his brother’s jeans dropped. 

 

“Right out here?” Cindy asked with a smile, peaking over at Lucifer and the door behind him.

 

“Right out here, baby.” Gabriel replied, sinking all seven hard inches into her sopping wet pussy. Their groans went right to Lucifer’s dick, and he had to start squeezing himself through his pants. Wasting no time, Gabe started to thrust inside her, deep and slow, causing her to moan and fling her arms around him, holding on for dear life. “You want a reason to hang on? I’ll give it to you.”

 

Lucifer was pretty sure he had the wrong idea about how to properly have sex, because even though Kelly had seemed to enjoy it well enough, that was nothing compared to what Cindy was going through. Gabriel’s hips were bucking forward at a startling pace, pistoning his cock in and out while the fingers of one hand played with the woman’s clit better than she’d ever played with it herself. She was practically screaming, the two of them sweaty and breathless as Lucifer palmed at himself, the archangels hearing someone enter the bathroom and ignoring it.

 

“Cindy?! What the hell?! What are you doing?!” the boyfriend of the woman Gabriel was currently railing asked incredulously. Both brothers just smirked, and Cindy made no move to stop the younger one from giving her another loud orgasm, Gabriel groaning as his dick was clamped down on. “Did you...did you just cum? You never cum from me fucking you.”

 

“Then how about you just shut up and watch, alright bud? You’re not the only one who could afford to learn a thing or two.” Lucifer suggested, and the man just looked at him, saw what he was doing, and looked back at Gabriel as he slowed down a bit to let Cindy recover. The woman let out beautiful noises that had her boyfriend swallowing as Gabriel kissed and bit at her neck. It took a minute, but eventually he slumped against the stall next to Lucifer as the lovers began to pick up the pace again.

 

“Go on, dude, whip it out. I don’t mind an active audience.” Gabriel said breathlessly as he started to really let loose, chasing his own orgasm as Cindy lied back and played with herself. She couldn’t stop dripping everywhere as Gabriel gripped her hips tight and gave it to her better than she’d had in years. Lucifer let out a small laugh, and Gabriel looked up at the mirror to see his brother staring at the boyfriend’s less than impressive cock, barely three inches long and skinny. The brother’s locked eyes in the mirror after that, and Gabriel just grinned as he got himself closer.

 

“Here it comes, baby.” Gabriel said with a loud moan, getting louder and watching Lucifer as the cum started up his shaft. The Devil blushed when his brother started to orgasm, the younger man never pausing for a second as he rammed himself home over and over again, filling his stolen hole until he was satisfied. He pulled out with a final grunt, smiling down at his handiwork. “Much obliged, darlin’. You want a piece of this, brother?”

 

“Tempting, but I’ll keep my pants on.” Lucifer said reluctantly. He wanted to fuck, damn his human vessel, but he wasn’t sure he could make himself do it in a place or circumstance like this. “But I guess I could join in a little.” he continued, walking over to where Cindy was lying down on the counter and only paused for a moment before he started kissing her, which she responded to eagerly. The boyfriend stepped up, but Gabriel just shook his head.

 

“Not so fast, amigo. If my brother’s not going, I’m going another round.” Gabriel said, helping Cindy up and only briefly interrupting his brother’s makeout session, only to turn her around and bend her over the counter. The boyfriend just stared helplessly as Gabriel’s cock filled her already full pussy, cum gushing out and dripping down his balls and her legs. Gabe grabbed her hair and started pounding away, the boyfriend looking pissed as Lucifer swooped in to resume kissing the unfaithful woman.

 

“But what about me? She’s my girlfriend!” he protested, but Gabriel just turned to him with a wink, not pausing his thrusts. 

 

“Trust me, by the time you get inside this pussy? You’re going to be thanking me.” Gabriel promised, turning back to watch his brother experiment with kissing while he slapped Cindy’s fine ass. 

 

It was easily another half hour of shifting positions, loud female screams, and another whopping load from Gabriel before the brothers called it a night. Cindy was bent over the counter, tired but extremely satisfied, with a huge smile on her face. The boyfriend hadn’t cum yet, and his cock was still hard as rock, but he just stared at the dripping, gaping hole presented to him while Gabe finished putting on his clothes. The Trickster bent down and retrieved his cowboy hat, putting it on with one hand and patting the man’s shoulder with the other. 

 

“Like I said, trust me. Consider it repayment for your trouble.” Gabriel said, ignoring the man’s confused and dubious look as the two brothers left, Gabe’s arm over Lucifer’s shoulder, leading them to the door. Both Cindy and her boyfriend cried out together, the archangels looking over to see them both staring at where they were joined, the boyfriend’s huge, eight inch cock sliding out of Cindy and making them gasp. They both looked up at Gabriel, who just winked again, and let himself and his brother out, reinforcing the grace keeping sound and intruders from interrupting anyone in the bathroom. 

 

“3...2...1...” Gabriel said, loud moans and wet sounds soon reaching their more sensitive ears, causing the Trickster to smile. “See? What’d I tell you? Fun. _And_ , fun without killing or hurting anyone. We got to humiliate a douchebag, fuck a gorgeous woman, ensure the two of them are gonna be satisfied for years to come, and do some brotherly bonding to boot.” he continued, Lucifer smiling in spite of himself, still buzzing with pleasure.

 

“It was alright. Could have been more blood, maybe a head or two exploding.” Lucifer said, the expression on Gabriel’s face causing him to make a placating gesture. “Alright, alright, it was...good. Is that all I have to do to get Jack to like me? Bang hot women and give their boyfriends giant dicks?”

 

“No, there’s a lot more to it than that, but it’s a start. I promise, Lucifer, humans are more fun and entertaining than you can imagine. You do your best to learn what I teach you, and I’ll do my best to get Jack to give you another shot. Sound fair?” Gabriel said, slapping some freshly conjured bills on the counter for the barkeep before leading them towards the door.

 

“Yeah...sure.” Lucifer said, looking at the barkeep as they were leaving. He subtly snapped his fingers, gold light flickering in his eyes and stopping the employee’s head from bursting like a ripe melon, the older man not noticing the attempt on his life as he counted the bills left to him in delight. He sighed, putting his hands in his pockets and following his younger brother into the night. 

**Notes for the Chapter:**

> I'm a gay guy, so hopefully I did alright writing out a scene with a woman in it. Apologies if not, but it's not exactly my forte. ;P Had a lot of fun imagining a womanizing Gabriel going at it though!


End file.
